My main concern is the cost of turning the property into a MTR especially with this being my first property.

The contractor will be your best resource to understand cost of the design; the earlier you identify value engineering opportunities, the cheaper it will cost to incorporate (Google: ‘Macleamy Curve’).

Florida home prices are high, and insurance costs are increasing.Management: Currently, I manage the property myself, which has been relatively easy.

If the property can be respectably sold for $250 you have to be all in at around $200 including the commission and carry cost.

Replacement cost.

The cost per unit is actually below average for Reno and maybe bit high for that location. 

Consider renovation costs and potential for adding value through improvements.Resources and Tools:Local Real Estate Networks: Connect with local real estate agents, property managers, and investors for insights into specific neighborhoods and market conditions.Online Tools: Use real estate websites and platforms to analyze property prices, rental yields, and neighborhood demographics.Tips for Canadian Investors:Tax Implications: Understand tax implications for Canadian investors owning U.S. property, including withholding taxes on rental income and capital gains.Legal and Financial Advice: Consult with a cross-border tax specialist and real estate attorney to navigate legal and financial aspects of investing in the U.S.If you would like to discuss further/need financing please feel free to reach out.

We took over the property management because the owner was having multiple issues with a few of the "tenants" that have illegally sublet the property, and we are now dealing with the ripple effects (e.g. squatters, dogs, dispute with neighbors etc.)The landlord is cash strapped, and has asked me to go in on the property/deal with him in order to get a cash infusion to cover legal fees & renovation costs. 

If the pricewould have been $20k less I would have been good with just a VA loan.So depending if you're looking at a larger more expensive house, I wouldn't refi the 1st one as I'm sure your interest rate is pretty low, plus adding closing cost would add more $ being refinanced.

In most cases your better off buying with "All Cash" and then you can use a "Delayed financing" program to get up to 80% cash back LTC loan to cost.