I’ve been manually scouring Zillow/MLS for deals, but it’s time-consuming, and I’d love to streamline this.2.Has anyone experimented with using machine learning models (like classifiers or regression models) to rate properties based on their condition from MLS listing photos?

I don’t really have an interest in House hacking if long-term rates are $700 a month incl utilities for a bedroom. 

If it's currently an STR they should be able to provide you with the p/l statement from prior years so you can see gross rents, operating expenses, average daily rates and occupancy levels.

This would allow you to maximize tax deductions at ordinary tax rates.

However, value add with a sale is not as implacted by rates.  

In this market, I would not finance a first time flipper at 75% profit split because the profits and success rate is lower than the last dozen years.  

Quote from @Scott Mac: It might be the investing environment.Right now we have a different interest rate picture then we had a few years ago.

Interest Rate: 6.5% per annum (fixed)5.

Taxes will still be owed on the boot plus depreciation recapture (approximately $105K taxed at a 25% rate).

Do you think this strategy gains strength if lets say... in five years interest rates are at 5.5 vs 7.5 now?