Some do but they typically offer lower LTV's when compared with HELOC's on primary residences. 

I wouldn't worry too much about the agent being the seller, but potentially try to do your own market analysis to make sure the selling price is comparable to others in the area.

So how it works in your county might be way different compared to other areas. 

If you're talking a coastal SoCal duplex, the answer is probably no...it will probably not be cash flow positive (assuming a mortgage on the property).In addition to looking at non-traditional types of property, there are also some lesser populated areas of SoCal. 

As part of your side of the story, try to show national data where rentals have increased over the past 20 years compared to ownership.

Rather than doing a Recast, if I invest the $50K into another SFH (at a price point that’s right for me) I’ll end up with $0-100 net monthly cashflow compared to my 3 other SFHs that are producing $2200/month net monthly cash flow (cumulatively).Based on the incredible growth going on in the Boise/Meridian Treasure Valley area (with an additional 400,000 new residents expected to move into the valley in the next 30 years) is it worth it to have a rental in my portfolio that is funding its expense but not netting anything to me?  

Find what other similar comparable properties are selling for.

Otherwise, non-medical HSA distributions are treated like Traditional IRA distributions in that they are taxed at the earned income rate.I'm not a tax specialist.

What insurance companies provide short-term rentals (Daily or monthly) insurance for Alaska properties and how do they compare on rates? 

I think we will just try to rent it the more traditional route as a yearly or monthly lease.