One key component is making sure there is language that outlines how the purchase price is reduced if a payment is received BEFORE the closing.

I am curious about any potential barriers to look out for- timing, access/cost supplies, labor force?

This reduces exit options and affects the value. 10) Small number of small units is the most expensive residential development there is.

@Mohammad MuradHouse hacking is a strategy to reduce living expenses and build property equity.

My wife and I don't want to follow the scale up construction company model (we already did and it wasn't the best).We do a lot of labor on our projects and are looking in to the future and realizing our bodies will not hold out over time.

If your property in Illinois is doing well, have you though about clustering around that to reduce your management costs.

This was a labor of love and there were so many unique and challenging aspects to the flip.

In your case though, I've heard of people in Denver proper with duplexes who parter with LTR tenants (you could put them in the basement) who will co-host with you and be able to get a STR permit since it's their primary residence and you can work out a profit split for the STR or some kind of reduced rent for your LTR in exchange for helping you and you being able to keep the STR runningJust a creative idea I wanted to toss out as a potential plan B or plan C!

If you sell the house, your repair and improvement costs will be added to the cost basis, reducing your taxable profit.

This approach can help keep your taxable income lower, thereby reducing your PSLF payment amount, which is calculated as 10% of your taxable income.