Combine that with insurance raising rates not just for dropping licensee count, but also to cover increased lawsuit risks.

You already have this covered.2.  

Since MTR is similar to both in different ways, you'll need a custom tech stack to cover all your needs. 

If you convert it to a rental and sell later, you may owe capital gains tax + depreciation recapture, unless using a 1031 exchange to defer taxes by reinvesting in multifamily.Leveraging $100K in equity via HELOC or cash-out refinance can help fund the next deal, but ensure rental cash flow covers debt, expenses, and reserves.

A fair entry point seems closer to $225,000-$250,000, but the terms of financing could justify going slightly higher if cash flow can cover the payments.

While real estate values do rise over time, if you can't cover your bills during the downturns to get you into better times to sell, you are likely to lose money.  

Taylor sent multiple email inquiries to our insurance provider asking what risks their policy covered.

If I rent it out and the rent monthly payment let's say covers the mortgage and HOA, the cash on cash return will be $40K(appreciation)/($ 42K (Down payment) = 95% and it will be 1.95 to find the cubit root and it is about 25% yearly return on my initial investment. 

Without taking a proper tour of the cabin and only driving by and seeing pictures of the inside.

Personally, I bought a 3 bed single family home soon after starting my job and had two friends from college rent which covered my mortgage plus a little extra.