This reminds me of how Alex Hormozie describes "the value equation"; Experience in this case is the factor that determines the likelihood of achievement. 1,000%Alex Hormozie is one of the greatest marketers not just alive, but ever. 

It's just not the reality.I don't know your wife's income so it's hard to know what you need to replace in order to let her retire but if you think you'll get her retired in the next year or 2....you will have a 99% chance of being let down.Becoming financially free, or not needing a 2 income household comes down to 2 simple factors.

Location and amenities are the two most important factors that bring potential renters to an STR. 

You can close in an LLC and don't need to provide employment history, income or tax returns, and DTI isn't a factor.

Most (not all) HELOCs require that the property is titled to an individual (not LLC) and are full doc, meaning your employment history, income, DTI etc will be factors.

Investing is different from speculating, in that it’s data driven and therefor predictable and you have factors that play in that covers your downside and strengthen your chance of upside. 

That said, if you have $50k and want to invest out of state, that puts your realistic budget at $150-175k...maybe even a bit less after you factor in closing costs, make ready expenses, and reserves.

Does that factor in both the mortgage, taxes and maintenance? 

HUD does not factor into the rent other amenities that might be included in the rent such as garage, basement, fieplace, central air, pool etc, that might command higher rent in the non-Section 8 market place. 

Factors that affect hourly rate Job complexity: More complex jobs may cost more.Handyman's experience: Less experienced handymen may charge less.Region: Some regions have higher labor rates.Minimum charge: Some handymen may charge a minimum fee for small jobs.Mileage: Some handymen may charge a mileage fee for jobs outside their service area.What to expect to payA handyman may charge between $35 and $80 per hour.