Plus the added tax benefits to support my current situation ($120k a year as a "single" person with "0" dependents Uncle Sam definitely gets his cut) A home my family and I could use in the off seasons on vacation plus creating a unique experience with lifelong memories for our guests sounds great to me, regardless of whether it cash flows.

These forums are a great place to learn and meet people, whether you're just starting out or you're a seasoned investor.

Id love to hear from seasoned investors or new like me!

Avoid escrowing payments and opt for the longer term, even if you don't think you'll need it.Seasoning Period: Many lenders have a seasoning period of 3 months on the platform, while others might require 6 months.

Ideally, I would STR it to either the wedding hall or seasonally, although the purpose of snow-birding is to be in CT in the summers (wedding season) and Florida for the winters.

To win as a first-time or seasoned house hacker who is ok with less space, you want to look for funky layouts.For example, a three bed and a one bed is a huge score because you can live in the small unit and make more money without room hacking or wasting space in your unit.

This would require you to satisfy the 12 months seasoning period. 

For insightful guidance, consult with seasoned investors, mentors, or real estate experts.

CPA recommended we open a joint business checking account under both of our names to keep tax season simple.

Partner with your lender ahead of time on this just in case they have some crazy seasoning or other requirements.