It felt like everyone I found were self-serving, looking to line their own pockets, or not willing guide because of fear of competition.

Here, in Portland, we have to offer an option for Appealing a denial.

Note these are only residential options. 

My vote is option one.  

**Cash-Out Refinance/HELOC:** Another option to avoid paying capital gains taxes is to not sell the house at all.

FHA gets a bad rap because sellers and many agents think it's only for people who don't have the money so if I had 20 percent, but wanted to use FHA, I would present a proof of funds with my offer showing I have more money, but am using the FHA as a financial option so I can get an investment property as well somewhere else.

Been listening to bigger pockets for about a month now (literally everyday, at every moment I have spare time LoL) and am learning a lot.

Your home needs to be in good shape (sounds like it is) and very competitively priced in order to have the few looking choose it instead of another option. 

Grab the books Multifamily Millionaire I and II from Bigger Pockets.

BrittanySelf-managing your STRs will keep that 20-25% in your pocket.