Chinking Wood Floors Before Painting...Suggestions?

The 200 y/o house I grew up in had manila rope wedged in between the floor boards. It made for an interesting looking floor.

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Just use floor leveler or mastic.

"....can you find a piece to just replace the board with hole..."

Ahh, tried that. Cut out a 2x3 section, but the depth wasn't 5/8 and it wasn't 1/2 inch but somewhere between. Can't find plywood that thickness. That's when I realized the tile on top of it all was just lifting up like a blanket off the floor. Really had no choice. I'm also trying desperately to avoid heavy sanding as it's winter and the place is sealed up.

There's product out called "Tavy Thin Skin" which is a fiberglass reinforced paper which you can glue to anything and apply tile on top - but again it would have cost about $300 to do the floor not including tile. So I'm just pecking at it....nice winter hobby....UGH!!

I've heard of the rope in the gaps too, jute twine and even oakum, but not sure I'd like appearance. I bought the caulk today. OSI Quad- permanently flexible. Comes in beige and it's paintable. I'll also use some of the old boards I've got around here to make wedges and pound them in the smaller cracks w/some glue and plane them down. It's the same material as the floors. 160 year old lumber! And when you cut into it, it still smells like a christmas tree! Fastastic old yellow pine. I kept the planks when they had the eves repaired on this building. I built a playhouse for the kids out of it, 20 years ago, tore it down last year and saved the lumber again! Now I'll use it in the floors!

"....Just use floor leveler or mastic...."

Nothin will stick to the Masonite! NOTHIN! It's shot! Masonite was abandoned 30 years ago for flooring because of that. It just doesn't hold up. 2 layers of tile lifting up like a blanket tells me the sub flooring's gotta go! And who among us would pass up a beautiful pine plank floor from the 1800's? It's just I didn't plan on all this! Guess it'll keep me off the streets til I can start planting my onions!

was more intended for the OP... but ya I'll agree...

You could look at how aces between boards on boat decks are traditionally filled.

Traditionally, boats were waterproofed by using Oakum which is jute rope teased into fibers, then soaked in oil and tar. It was wedged into the gaps between the planks. When it hit water, it expanded and created a waterproof seal. Great for boats, but I don't want that oil/tar smell in the house. So, here's a suggestion:
OSI QUAD sealant. They have it at Lowe's and Menard's. It's for exterior and it's mineral spirits cleanup. It dries elastic - never hardens, but I've seen recommendations for using it on flooring gaps too. You should probably use painters tape on the boards on each side so you can keep the line straight and the adjacent boards clean. That's what I intend to use. It comes in several colors including brown, beige and tan, white and clear.

Update on my floor: I've got most of it scraped (what a job) and I've decided to stain and finish the wood instead of painting. I figure I can always paint, but once I paint, I can never get back to that natural look. So it's stain/finish first, see how it holds up and if it doesn't, I can paint it later.
** Surprise! I found a 'treasure box' in the floor. A couple of planks had been cut out under where the wood stove once sat. Nothing inside but a pearl button and a bullet casing, but definitely a hiding place where I'm sure they stored their loot before banks were available. I have also run across a lot of buckshot in the cracks of the boards. Guess he filled his shells there too. Very cool! It's going fast. I'm figuring March it should be done.

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I was looking at the floors and wondering if they had a Subfloor to hold chinking. I'm wondering this because at our Homestead we used Green Oak for the floors which dried and left a gap, we tried everything over the years never found anything that wouldn't fall through. You wouldn't have this problem with Log Homes because chinking would be resting on the lower Log holding it there.

We finally had to put floor over this floor.

big rockpile

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I saw a number of videos on floor restoration which were handling floor boards that were straight sided. Mine is tongue and groove. The only real way to fix a tongue and groove floor is to re-lay it to eliminate the gaps.

In England, on straight sided boards, they use "pine slivers" -google it for a video. they're long (18-24") wedges which are glued and pounded into the cracks, then planed and sanded flush. I made my own cuz you can't buy them here.
Even tho I have tongue and groove, I'm still going to experiment with these wedges in places. Most of the gaps will be filled with the OSI caulk.