I keep hearing that STRs are dead and that Airbnb/Vrbo will be a bust, but I can't help but think that there are other factors that are somewhat contributing to this thought, such as people getting into the STR game not know what they are doing, defaults due to communities putting in heavy restrictions on STRs, etc.

@Steve Smith I know using self-directed retirement accounts is pushed pretty big, but my understanding from accountants including my own is that people tend to get themselves into hot water with them. 

Will it automatically just be included to the deed and title of the existing home?

I own 2 older townhomes, and there are constant assessments (including $6000 each for roofs) and fee increases.These issues aren’t always apparent from reading restrictive covenants and seller disclosures so it’s important to verify with the HOA.

Early investments into your business will include marketing, software, MLS dues, education/coaching/mentorship, gas/mileage/travel, taking potential clients out for lunch/coffee, etc.When you're not working at your PT job, focus your time an attention on the following:- everything @Dallas Sauer & @Hayden McDougal mentioned- Having conversations with 5-10 people everyday.

We use a management software that includes tenant and owner portals. 

And maybe Disneyworld .So i can see cost being a major factor to the STR business in and around Disneyworldd.

Determining exactly how beneficial is based on a multitude of factors, but a cost segregation study cost/benefit analysis on your property is typically free and can help you decide whether the benefits offset the cost of the study.If a Cost Segregation Study had not been performed on this $560,000 single family home located in Phoenix, Arizona, it would have had first year depreciation of approximately $20,400.

Guests are responsible for their own utilities and housekeeping expenses.Renter pays for all utilities including water, electric and gas.

One property manager (10%) is more flexible and says that I can get away with 100-150K of rennovations (including pool which is 80K), whereas the other (20%) property manager says I would need to do 200K to get the returns I'm looking for.