Here are some of the downside I can think of: 1) PMI costs, til 20% LTV2) over-leveraged with larger mortgage payment (more difficult to cash flow) 3) no refi until at least 20%3) other?

That's the value of the business component of the sale.In larger companies (roughly $10M+) , there is a different method called EBITDA - earnings before interest, taxes, depreciation and amortization.To that SDE value, we add the value of assets (vehicles, machinery, etc) and real estate, if any is to transact. 

Marketing I've done: Listed property w/ local property managers - they post on MLS and syndicates to Zillow, apts.com and craigslistI'm posting myself in off-campus forums and forwarding qualified applicants to property managers for showings April 15-30th (when I didn't have the property managers)8-10 showings mostly off Zillow/FB~3 Applications0 qualified renters/0 tenants bookedMay Stats:9 or 10 showings 4 applications1 tenant booked in unit #1There are 2 remaining units, unit 2 and 3, which were initially priced higher than unit #1 because they are slightly larger -- That said, I'm thinking that I reduce prices and take advantage of the higher demand in the coming months...Does this answer your question?

Helocs are also nice because that equity is there when you're ready to use it, but you don't have to lock yourself into 30 years of larger payments on day one. 

Capture the liquidity/equity of the asset, buy another property with it, and keep the original property.

These are cabins in the woods, so we have issues like power outages, neighbor's construction noises, internet outages (a big deal when people are planning to "work from home" at the cabin), guest thought they reserved two nights when it was only one, cleaner forgets to show up... all sorts of things that add up.It seems like the littlest issue gets compounded into much larger issues that cost us lots of money.

If you sell the property be mindful that there are actual costs to sell since the asset is not liquid.

There is definitely enough space to build something larger (multifamily), but it probably isn't zone for that.

@Christopher Lee to my knowledge this is not a common thing, it may be that being based somewhere else allows larger cases to be handled in courts in states more favorable to landlords, but most cases (if you have any) will not rise to that level and likely not be worth the additional fees of setting up and maintaining the structure. 

I've seen posts that use larger funds as an example i.e. 30MM+.