I'm contemplating doing a 1031 exchange on an SFR and using the proceeds to buy a vacation condo that I will do STR's on for at least 3/4 of the year.

Is there a way to circumvent the employment history in order to obtain conventional financing (besides getting a co-signer), or should I start contemplating alternative ways to finance my investment?

@Jessenia Munoz Thank you for the post, this is the same sort of question I have been contemplating for quite a while now.

I'm contemplating at least putting up drywall or cleaning the space up a bit for future showings.  

So If your are still contemplating this as a rental I would definitely raise the vacancy to about 1.5-2 x's the monthly rent.

I am contemplating on going the FHA route but would like to have a better understanding of issues I may encounter. 

This hypothetical best rate but slowest process lender is going to make you contemplate suicide with the hoops they make you jump through.Do not try to generalize based on those three scenarios.

I am contemplating just such a thing in the next year. 

Junior liens have some considerations to contemplate due to the priority in title they hold.  

Not happy about that, and coupled with other issues, i'm seriously contemplating taking this over myself.