If renovating adding the story would increase the rent significantly and make it more in line with the neighboring houses it may be worth it.

And if your investor friend’s private loan helps fill in any gaps, it might be worth considering that short-term pain for long-term stability.What do you think you’d focus on first... paying off that line of credit as fast as possible or jumpstarting the renovation to boost cash flow right away? 

It takes longer to realize, but the gain is worth so much more than a couple hundred dollars of cash flow a month.

. - the juice isn't worth the squeeze to me on that type of loan product.

It also means thinking ahead (will this home be a good rental if/when I move out, will this home have good resale if I need to sell it at any point). 

Yes, the bi-yearly nit picky inspections can drive me crazy, (torn screen , etc) but in the long run it’s worth it.

True, but that doesn't mean the other people there aren't worth meeting. 

It would leave your net worth really skewed into one asset and class of asset. 

It’s a short term rental started in Oct 2024 and earning during this off season is under $10K but cost segregation has nothing to do with rental income only depreciation of the property and with bonus depreciation being 60% this year I think it’s worth it.

@Marc ShinAbsolutely.Board games are not that expensive and are worth adding.I see cable TV channels as a must along with smart TVs.