Treasury bills are paying 5% and if you stagger their maturity you could have the money ready to go if you find a better opportunity.

My CPA is saying I have to pro rate those expenses for the number of nights that it was actually rented out, but I can't find anything online that confirms that.

Sam - did you ever find a more cost effective solution to this than SaniStar?

House hacking with the first property would be nice if I can find the correct space and deal. 

It just a matter of finding which fits your current situation and future growth.

Find out who is their daily pontoon insurance carrier.

Find a partner to fund the project, find a contractor, work out terms that are favorable for all parties, bring something special to the table and get higher rents because the property is nice an shiny. 

I find is so much joy when I find my clients great deals.

It doesn't change ownership, just trustees.Talking to an estate planner, a good cpa, etc. will help you find a solid solution. 

You can find off market deals in any of the following methods you mentioned.