I’d say if buying something to live in is an option, I would go that route.

The players won't inject money into the local economy as they make peanuts, fans won't come out in droves to see it, and there won't be an economic windfall from bringing the team in. I

The market I stick in is the 14k-75k rental market.

Like the stock market the Real -estate seems complex breaking rules that have been followed in the past.The area I am in is still a sellers’ market priced right an offer on the first day maybe 2.SFH for rent are renting in the same fashion that I have never seen!

I wasn't thinking of using the STR as income qualification for future deals necessarily, just was wondering if getting a loan on an investment property based on rents that a long term rental would bring in is the way to finance an STR without going the vacation home loan route.

Or, given the high property values in the market I''m in, is it better to hold onto the property and rent it out, even if it costs me a bit out of pocket, to continue to gain that appreciation and the knowledge of having that first investment property? 

Like X in Y homes you'll lose to others without contingencies for example.

I used this to help me look at comps and after I put the numbers in, I knew it was not a good deal for me as the property was overvalued.   

Time to get in is now. 

When I have found a property I am interested in, I usually reach out to the agent that the website has and ask for details.I’ve also worked with an agent that was helping me get information about another property I was interested in as well but I didn’t enjoy how I was getting second hand information and sometimes I’d get mix messaging.