That kind of restriction just doesn’t work for someone like me.I’m trying to figure out if I might be missing something in how I’m approaching this or if others have insights or examples of towns that not only allow STRs but also have laws that offer enough flexibility to operate in the way I’m aiming for.Many towns technically permit STRs but impose restrictive rules like membership requirements, ownership duration limits, or rental day caps, making operations challenging.

The guy is genuine in his approach and really does help people get across the goal line.

The property cash flows and I could definitely see each investor making at least $1000/mo with the most hands-off approach of renting to an operator and much more if a person ran it as STR or LTR and it is a great diversification play for me as Costa Rica should see much better appreciation than the Midwest, but if I were to cash out I could see five times the cash flow because of the power of leverage.But I think you hit the nail on the head in saying that it is a lifestyle type of investment.  

Figure rates are significantly higher doing this instead of the more straight forward approach.  

What about drive approaches, parking lots, site lights, landscape, irrigation, etc.? 

I would at least start there and good timing to figure out a plan with spring slowly approaching and our busier sales season in WI.  

So- in your approach, I would not mention that at all.

What are your thoughts on this approach?

I’m seeking guidance on how best to approach this situation and would appreciate your thoughts on what you would do if you were in my shoes.Here are the details: My current home loan is $242,000, and the property is estimated to be worth approximately $420,000 (± $5,000).

This approach ensures that we have the ability to appropriately maintain a community, ensuring its long-term viability.