The money that you end up owing to repay the loan over the 5 year term is now post income tax money unlike how you traditionally are supplying your 401k with pre-tax money.  

That being said rents have flattened mainly because of the supply of new construction in the area. 

A lot of lenders used to apply 35% for expenses, but in the last several years, the numbers for supplies, labor, utilities, taxes, etc… have increased significantly.Also take into account the age, occupancy and how has the property been maintained, this will affect the expenses too

However, the broader structural issues of affordability, housing supply, and financing access will continue to shape the market in the years ahead.For now, the homebuying process remains a challenge for many in this generation.

In my case, all three sellers were older and tired of dealing with tenants, but they liked the steady income.

That way, they get steady income, and you avoid a big down payment.

After 12 years of accepting my full time investor lifestyle - with high income and liquidity events some years and no income others, my wife told me she was burnt out on the psychological ups and down and asked if I would consider just getting a job with a steady paycheck.  

Someone to stock supplies, an appliance repair person, heating/air conditioning repair, plumber, lawn care person, carpenter, salesman, and occasionally an electrician. 

Manage their properties Provide welcome gifts/ goodie bags for their guests before check in Hauling extra supplies/ misc items to return to stores or other properties--Any other ideas that I can pitch to make myself more marketable?

Emphasize how this arrangement could work to their benefit, offering steady income, avoiding a traditional sale process, and giving them the freedom to move forward with their plans such as buying that sailboat and sailing around the world.If they ultimately decide they’re not interested in selling, you’re still in a great position to continue your search and buy your own property in the near future.