Additionally, many FTHB programs are stringent with how much income your household is allowed to generate in order to qualify. 

I wouldn't wait as you will be spending money on rent so buying a property typically lowers your expenses not increases them, maybe avoid doing a big rehab project though, etc. find something instead good shape. 

Read some books, spend times on the forums, listen to podcasts.

Even if you can reduce the amount you're spending in rent right now (3.1k), you can still be a part of the appreciation play (although I wouldn't hold that as the main driver). 

This will not work and apps will just help you generate minimal activity that you don't have time to respond to anyway so I would spend more time figuring out how much time you can square away for REI.

Its your money to spend on STR, etc.Read your documents, but Loan Agreement would specify.

I am not sure if partnering with close friend, also with 50% stake in the game when I may have to spend more time on this whole process sounds fair or not.

However afterwards you might need to spend more money for maintenance.

I've done a decent amount of research into these markets but also spend a lot of my free time just reading every article I can find about the best vacation rental markets in the country and also reading through these forums to see what other people are saying.

If you plan on holding forever, you can very likely be spending large sums of money every 10-15 years for kitchen and bath remodels, all new flooring, etc.Lastly, a 10% vacancy implies you will be down about 6 weeks after each 12 month lease.