I just like to list places and keep them posted so I get a chance to talk to nice new people, like you.

you say they have insurance for their pet,, they need to give you a copy of that and you need to verify with company policy is up to date, give a copy of that to your ins company and let them know your working to have them move out and have given them notice to do just that. 

I would prefer to pay the capital gains today as based on how we spend money as a country, that capital gains rate most likely is going to be heading up in the future not down.

Is it foolish to consider using the HELOC for the down payment?

Purchasing a STR in a somewhat sketch area is a terrible idea and as others have mentioned, is going to open you up to potential issues. 

Would like to be in a city where I could get potentially $1,500 to 2k in rent.

looking to do a quit claim deed .

I'm not trying to be hyperbolic. 

@Elizabeth King Your property does not need to be in an LLC to benefit from real estate tax advantages.

Similarly, if you put several Class D tenants in a Class A 4-plex, what do you think will happen to the property?