Real estate can provide a more tangible asset and potential for rental income, but it requires more management and can be less liquid.

Profitability can also be enhanced on a sale (sometimes) if we choose to provide owner financing or wrap financing.  

Overall, providing the option to buy in the lease can be a great opportunity for both you and tenant; provided the quality of the tenant.

The good news is that real estate can provide you with the lifestyle that you are describing: No 9-5, cars, travel, financial freedom, etc. 

I recommended using the safety hazard approach.

Additionally, seeking mentorship can provide invaluable guidance as you navigate this new venture.

You say you think the make sense, but you don't actually provide them.2) Second position?

I'm a software developer and very good with a spreadsheet and all, but I'm wondering if I could secure an experienced lender who not only can lend, but also provide advice on a deal like this from having financed similar situations before.Pointers to financial calculators for such an endevour and hotel/motel renovation-style lenders & contacts appreciated.Thanks,Matthew

They provide a format for calculating the bid but no real directions with it.

An additional benefit of a detailed engineering-based Cost Segregation Study is that it can increase potential insurance premium savings as well as provide support for the property tax appeals process.