This could mean investing in property flips or purchasing out-of-state rentals for more stable income, but it would require letting go of the $1,350 rental income from the manufactured home.What factors should I consider for each option, and how would an experienced investor assess this situation mathematically?

Once you've pinpointed your objectives, it's important to assess your financial situation.

I've seen active pump jacks in the yard, but not sure who was there first...the well or the house. 

For example, you buy a house for $1,000,000 but you say you bought it for $100,000How do they find out how much you paid for a house to assess their tax?

Networking is key, and places like Facebook groups, BiggerPockets, and REI meetups are perfect for finding active cash buyers.

If you look at the tax assessment, there will be an assessed value and the taxable value. 

So typically passive activity losses are grouped together and carried forward to offset other passive activity losses if your income is over 150k.

Do you have a nice amount saved up for the activities you enjoy(I assume yes given a 30+ year in Tech plus you mentioning making lots of money already in real estate).If that is the case, what are you looking to achieve now within real estate?

Get detailed quotes on these to ensure it’s cost-effective.Zoning & Permits: Verify that your current property allows additional homes and meets zoning requirements for multiple units.Rental Demand & ROI: Assess demand for singlewide rentals in your area to confirm it’ll be profitable after all expenses.If everything checks out, these could be solid additions to your portfolio.

I am a big advocate of home ownership, but in the situation you are describing (not knowing how soon you would leave), it might not make the most sense to buy a condo with restrictions or potential assessments in the future.