I have a 5/2.5 house that is close to Tyndall and was debating on renting to single family or possibly renting out rooms individually to single enlisted members(almost like college housing).

The other four only allowed for a one time late fee. 

There's also a law that HOAs are not allowed to regulate property use in any way, meaning they can't tell you that you can't have an STR or LTR. 

CA Law allows for the construction of an ADU.

$6,100 PITI + Maintenance, Cap Ex, & vacancy reserves Versus whatever similar rent would be in the area.If you're okay with this deal not being a homerun initially, but allowing you to live in an ideal location in a nice home with slightly less mortgage cost, then it may be worth it. 

I am looking to create a system which will allow me to analyze and choose markets more efficiently.I want to have a pool of resources/websites that I follow step by step so for example, 1: Check the housing prices, 2: Check the population, 3: Unemployment rate, etc... and then I will pull this data from the websites that provide it and keep going down the checklist.

This mitigates the risk for the buyer and allows things to get wrapped up quickly.

since I was under the $250k cap gains for individual - I just didn't think past that! 

It will be easier and cheaper to obtain than Hard Money and you may be able to keep the loan for 2-5 years without re-financing which will allow the property to appreciate.

I've had such bad experiences in the past with dogs in a different fully furnished short term rental where we originally allowed dogs-- swimming in a decorative pond and disconnecting the filter, killing the koi, chewing up a couch and other soft furnishings, scratching a newly installed hardwood door and ruining the finish, digging giant holes in the yard and landscaping.... thousands of dollars of damage, really, in a very short time, which is why I have a strict no pets policy, and am particularly nervous about dogs on the property.