I understand it could be a problem if I were making offers and holding up the process often if I couldn't actually get HML loans, but my intentions are to only make offers I know I can back up. 

I know you said you are from there but have you done a market analysis to back up your assumptions on the future of the market?  

I'm just saying that if I had to go per-person for whatever reason, I have that as backup.

House popped back up on hud for one day and I grabbed it.Sometimes its just a matter of lucky timing. 

Suggest you look for a backup GC.

However, some of them don't require a lease in place and can use market rents.Even if you are using the property for STR, you should always have a back-up, and a good one to fall back on is to turn it into a long-term rental that will cashflow.

The new construction market (at least in my area) is booming so I may be seeing things from a different lens than most, but I believe things will pick back up next year as they seem to normally do.

So I have a back up property that I’m looking at Incase my first offer falls apart.

(I'm running into this with my 3/2 STR outside a national park - booked solid all summer, but once school started back up, demand for that many beds dropped off, and I had to figure out how to attract more couples to fill the gaps)Once you've got a decent idea of vacancy, crunch the numbers to see what kind of ROI you can expect on a big house like that vs. something smaller.  

(normally recommended, especially if you are a landlord)- Water Backup: For water damage due to the backup of Sewers or Drains.- Personal Articles: Coverage for belongings that have a special or collectors valuesuch as Jewelery, Furs, Fine Arts, Collectibles, etc...Your age should not be a factor on the pricing but, depending on the company these other factors may get you credits:- Insurance Score (company pulls certain info out of your credit report)It is not your credit score but generally better credit will result in a better score- Time at your job- Education level- time at current residence Good Luck