I listen to the podcast pretty regularly and have been spending a lot of time on the forums trying to gain information.

This was the cheapest option I looked at (through USAA) but not the best coverage if you are serious about hosting. 

If you apply it on a regular basis, then you'll eventually see the results.

I host a little blog right here on BP that you might find helpful:https://www.biggerpockets.com/member-blogs/3915/86269-self-storage-investing-how-to-figure-out-if-its-a-deal 

High risk, but potential for a more lucrative investment.I've reached out to a couple airbnb hosts in the area to see what they are averaging for monthly income on similar units (1950's build and updated interiors), and the range is $2,000-$2,600.

Then they cost SO MUCH to replace.  2 of the 3 buildings have boilers that are regularly maintained.

I'd rather get a regular loan and then use an unsecured line of credit for the renovations (then refinance out the money needed to pay that down). 

Another option is to get a line of credit either from a HELOC on your primary or an unsecured LOC and then refi to a regular loan when the property is in good shape.Post about what the hard money lenders offer and the forum can tell you if they offer a fair rate.

Have to assume the host thinks they can get what they're asking for the dates that aren't booked.

They have a lot of resources that are available 24/7 and then I believe they have webinars regularly.