Buy a property when it feels good is when you are buying your primary home where your kids will grow up and you'll live with your family.

Need some advice.I do some small private money lending to home flippers.

Also, the term "house hacking" is generally used for your owner occupied home (renting out rooms in your primary home) and that income cannot be used to help you qualify (it is considered boarder income). 

However, my debt to income ratio with that home loan, and student loan doesn't look that great currently and I don’t have much for a down payment.

I am currently purchasing a home that will work great as a Rent By the Room. 8 bed and 6 baths in the DFW area.

I generally look for two things: new homes on the market for sale are they being sold very close to asking price, with short days on markets or not.

Imagine a 4bed/2bath home with a small ADU in back, a converted garage with a private entrance, or a three-level home with a basement that can be converted into a private apartment.You can get privacy and house hack, but it takes a little more effort.

(particularly true for single family homes)  Tom and Aaron may have different experiences.  

very sorry to hear that. a lot of "professional" unfortunately only look at you as a number and not a long term relationship. you should be able to put a complaint against home inspector to hopefully recover some damage they missed

Most desirable areas in Tampa Bay are in AE or higher risk flood zones and generally sell for a premium for a comparable home placed elsewhere - all else equal .