You should be able to get up to 80% LTV on a rate term refinance.

As you go on your real estate journeySomething I would recommend for you is this website. https://www.areavibes.com/Use this rating and classification system I have created over time to get an idea of the "Class" for the area - A class B class & so onHere is my rating & classification for each livability score.80 and above A+78/79 A76/77 A-74/75 B+72/73 B70/71 B-68/69 C+66/67 C64/65 C-60/63 D59 and below F

Question: Should I collateralize the loan (if using private or hard money), or rely on roll-over loans (to maximize the lower points and 3-4% rate)?

Interest rate- prime plus? 

To add to your argument I suppose the tax implications are better with RE too bc theres a capital gains tax ceiling of 20% vs standard tax rates for IRA withdrawals that are potentially much higher.

A great lake front home doesn't have to cost a mint but it sounds like you want something that is really fantastic which will bring a higher nightly rate.

Hosts can get involved by either donating a portion of rents from their payouts or they can offer housing at a discounted rate.

At any rate it is possible, but depending on your appraisal it could be a gamble

I looked at the rental trend over the past 10 years, I should be fine in year 7 for the refinance unless rates are totally out of this world.Your right those rents would be really low for Stamford. 

Higher inflation equals higher interest rates.