For this property, you would be wise to incorporate the income from the other units against your debt service to make the property more attractive to lend on.

Once you do that then in any area 3 things will determine if you will have better revenue and better results than your competition. 1-design 2-Photographs 3-listing optimization.I just had a client purchase in seattle a few months back and the listing we created is the best one in the area and is on pace to do better revenue wise than the others because we did those three things and made the listing stand out. 

Even if it is mid winter, you could always do an 8 month lease that rolls into a year long lease in August, setting you up for future success, timing wise. 

car broke down the last time I heard that one was in the Morris invest debacle @James Wise has chronicled. 

Education wise can be expensive depending on how a host has gone about learning how to run a STR.

Another rental house breaks even cash-flow wise (+$100/mo),  but pays down $500/mo. 

For financing, check out local banks, credit unions, and online lenders for investment property loans.Considering an LLC is wise for asset protection.

Wise investors are putting systems in place (including property managers and other service providers) so that these risks are mitigated without investor being involved.

If you worry about trying to figure out the best option right now, you will more than likely spin in circles trying to decide if can be an STR and if it can be an STR, is that better than an LTR cash flow-wise and time-wise...and should you manage it...should you hire it out.

Nancy Reagan should have been a guru…..Let’s follow her wise teachingsGo to your Real Estate Investment Association meetings… stand up and Ask…” HOW DOES THIS DEAL COMPLY WITH WHAT …ALLLLL … OF US WERE TAUGHT”how is this a dealHow is this a dealThe quote NancyJUST SAY ..NO !