My current policy with Pillar Insurance is EXTREMELY high ($4k-ish), including a $2K Hurricane Premium on top of the $2K Non-hurricane premium.

I don't know of anyone that would take on a recourse (or even a non-recourse) loan with someone who has no skin in the game.

With or without leverage, through non-recourse loans and the potential UBIT?

Long story short(ish), I would caution anyone who is going to make any large non-permitted, structural improvements to a house they plan to sell.

You must use non recourse loan meaning no personal guarantee.

Medical tenants have heavy TI when they go in so if building is really outdated and old they may leave to a new building completed by a developer with all the new bells and whistles unless you just have the best spot in town already. 

We are analyzing a purchase near Vista and our partner on this effort looked up the following:1. https://www.airbnb.com/rooms/14292365: Small studio rental in same area; historic converted carriage / barn = $100/night with 14 nights booked so far in May = $1400 for month2. https://www.airbnb.com/rooms/9351161: 2bd/1ba guesthouse same area; non-historic and bland = ~$95/night with 24 nights booked so far in May = $2280 for month3. https://www.airbnb.com/rooms/17674810: 1bd/1ba same area; non-historic but well designed = ~$90/night with 19 nights booked so far in June = $1710 for monthYou probably would want to do more similar analysis on Vista before proceeding with the STR route. 

So here we missed one payment in this example, but our credit report actually shows 3x30 day lates.Like @Harjeet Bhatti said, you're probably cut off from the gov't subsidized Fannie/Freddie stuff for an investment property for a year or so.However if you come across something, and it's such a screaming deal at that price that it still makes sense even with non-ideal financing (remember that if you have to choose between the two, killer price is better than killer rate -- as any successful flipper will attest to), there's a lot of "Alt-A" (once upon a time called "sub prime") that's come out just in the last year that's better than HML.

I also just replaced a boiler and instead of using their financing- I used the energy financing program through my power company- They have a 10 yr O% financing program and it’s even for non owner occupants.

The only reason I am hung up on this property is because the interior is very nice, and the location is quite convenient (right across the street from the medical district which is the heart and soul of my community).