Two high level quotes come to mind "Let your winners ride" and "a great value asset at a fair price is much better than a fair value asset at a great price".

I'm thinking it's better to rent the entire property vs a room.

Appreciate the info on the One PIN as it should help us explain to the lenders better (who aren't Alex!)

- What types of properties are better for cash flow?

Even had him pay his friends who would help so he understood people better.  

My best advice is the manage the debt better on property #2(as in recast this), evaluate rent appreciation on #1 and depending on income if you do buy a primary-- you better pay cash.

Additionally, explore alternative financing options or strategies that may better align with your long-term investment strategy.If you decide to pursue a hard money loan, research local hard money lenders in Virginia, and consider reaching out to multiple lenders to compare terms and rates.

You’re better off just putting the $500k in a cd and getting paid $2k/mo in interest and spending $100 of that on insurance. 

This property couldn't have a better location and its charm was evident.

You'll get better price points on a distressed properties without the competition.  2.