It's crucial to evaluate how the deal performs with the new mortgage:Updated Financials After Refinancing: Market Value: $250,000 Mortgage Amount (80% LTV): $200,000 Equity: $50,000 Interest Rate: 5% (30-Year Amortization) Assuming after 12months the rate will drop from 6% to 5%Monthly Expenses: Mortgage Payment: $1,074 Property Tax: $260 (4% Adjustment from last year) Utilities: $309 (+3% Adjustment) Insurance: $104 (+4% Adjustment) Vacancy: $105 Repairs & Maintenance: $105 (now after 12 months we can assume we have repairs at 5% factor on annual rent) Total Monthly Expenses: $1,957Rent Income after 12 months assuming annual rent increase at 5% : $2,100Cash Flow: $143 per month 😊Year 2 Return on investment $2,951 Principal Paydown year 2 $20,000 Property Appreciation (assuming 8% per year) $1,720 Yearly Cash Flow (this will increase as rents rise) $50,000 Initial Equity Total Gain $74,671 with just $ $22,789 remaining in the deal. 

Ensure you thoroughly evaluate the lease terms and have a strategy to manage potential delays in finding a buyer.Best regards, Stevan

It’s always insightful to hear how others approach raising money and evaluate those who do.

And cash flow negative is a function simply of the leverage in a deal, you can be CF positive you just need to leave more cash in the deal and it's worth it for a better property.Completely different way of looking at things and you're going to be forced to evaluate like this in a new higher rate era plus housing scarcity.

Could you provide insights on how to evaluate whether this is a viable strategy?

Go out in society and evaluate how many have done it.

It’s a lot to keep track of, especially when researching multiple markets.Would greatly appreciate any advice/insights from experienced investors who've navigated these challenges :- How do you approach understanding and evaluating short-term rental regulations when considering a new market?

You really need to know your numbers well and build in some good cushion.Tools I use to evaluate rentals and loans.  1.

You need to know how to analyze property and then systematically evaluate property on a daily or weekly basis to stay on top of the market. 

Armed with this information, carefully evaluate whether the numbers meet your investment objectives before making a decision.Good Luck!