I find that automation often adds more complexity and time to a given situation rather than helping you save time.

we just managed to get ong to run all new lines and separate meters for our whole apartment complex at no cost to us. 

.- Can't see a Senior-Only complex allowing Short-Term-Rentals (STR).If so, SELL.2) What is the history of Association Fee increases and how well capitalized is the Association for future repairs?

Get your basic estate docs in place before building a complex entity structure.  

I'm considering using hard money lenders or DSCR loans, but it seems like DSCR would be a bit complex.

Mortgage recasting is a great option for homeowners who:Have received a windfall, such as a bonus, inheritance, or proceeds from selling another property.Want to lower their monthly payments without extending their loan term or going through the hassle of refinancing.Are satisfied with their current interest rate and loan terms.How to Get StartedIf you’re considering mortgage recasting, here are the steps to take:Contact Your Lender: Ask if they offer mortgage recasting and confirm your loan’s eligibility.Determine the Lump Sum Amount: Decide how much you can afford to put toward your principal.Calculate Potential Savings: Use an online mortgage calculator or consult with your lender to estimate your new monthly payment and total savings.Submit the Request: Once you’ve made the lump sum payment, your lender will process the recasting and provide a new payment schedule.Final ThoughtsMortgage recasting can be a powerful tool for homeowners looking to reduce their monthly payments and save on interest without the cost and complexity of refinancing.

You have two unrelated questions here.Question 1My impressions of your LLC setup is that having the ownership change over time is too complex with the potential for misunderstanding. 

@Ashly FrassoRenting by the room can be a profitable but complex model.

. - Based on sale of other units in the complex, I believe my current equity to be roughly $160,000, a little more than 50% equity. - The condo is currently leased through April 30, 2025. - August 2025 will be 3 years since I moved out.

You can take out a lot of complexity when you buy property that only needs maye paint & carpet.