Would it be worth seeking a free consultation with a real estate attorney to evaluate my case?

I was lucky to split the sales over 2 years, so the first ~80k gain is tax free and 80-480k was at 15%, which I was able to take advantage of twice.

Also, if you’re a private lender yourself, feel free to chime in—I’d love to hear from you!

You can get some estimates from contractors for what they charge for big ticket items like to renovate a bathroom, renovate a kitchen, replace the furnace, replace the roof, etc.All wholesale deals should have free and clear title and you should be able to see the sales agreement before submitting the earnest money deposit.

There could be a "double whammy", a recession (which we seem overdue for) then a drop in interest rates which leads to a big influx of new housing supply. 

Feel free to call me.

What leads to the highest repair cost? 

@Federico Dallo you mentioning vacation-type locations leads me to guess that you may want to use the property yourself occassionlly?

Unfortunately, usually when people get something for free they don't value it.  

If done right most of these gains are tax-free- $40K in equity capture (profit) with $20K out of pocket and 13% cash on cash thereafter (300%+ returns)- $24K of equity capture with $32K out of pocket and 36% cash on cash returns thereafter (75%+ returns)- $41K of equity capture with $27K out of pocket and 12% cash on cash returns thereafter (150%+ returns)None of the above numbers include loan pay-down or appreciation.