If you're able to save $50-100K per year for 14 years (when you're 40), a combination of getting solid deals, paying down debt, and having a target goal of income vs expenses, it's definitely doable.  

The primary requirement is that the expected rent would cover the mortgage on the home - and that expected rent is typically determined by a combination of the appraiser and some service like airdna (a site which determines fair market rent).

Showcase real-life success stories and emphasize how real estate income, combined with tax savings (e.g., deductions, 1031 exchanges), could potentially outweigh your current W-2 salary over time.Suggest a trial period for the first deal, involving him in decisions to build trust and confidence in the process.

I have three listings, 1. unit with a pool and hot tub, 2. unit with a hot tub, 3. both units together as a 12 sleeper.Gross monthly income (after booking channel fees) for the first unit over a 7 month period was $7309.Gross monthly income for both units over a 14 month period is $11,297 (after booking channel fees) As a long term rental the combined rent would be in the region of $5500.Is it possible to sell the property based on the income generated by the STR business or would the value always be based on bricks and mortar comps? 

It's probably 300k maximum for the combination of 3 and I have to get them re-appraised.

I think I've bought 10 houses (primaries and investments), and I've had that same "Oh crap, my chest hurts, why did I think this was a good idea?"

A friend of mine invested in one last year—apartments upstairs, a small coffee shop downstairs - and the combination of income streams made it a steady performer.Scaling with a 1031 Exchange:While not applicable unless you sell a property, planning for a 1031 exchange could help you scale quickly while avoiding capital gains taxes.

The goal is to keep these for rentals.I currently own the land personally and am funding the builds with a combination of HELOC and cash - no bank debt tied to these properties specifically.

They are either a combination of a Maintenance/Tenant Management business or Accounting/Real Estate sales/Tenant management service. 

I'm Francisco Centeno (REALTOR)So, cost segregation is basically deducting the depreciation of a property for years.Now, in the hypothetically situation...If both of you combines were earning $700k and you just bought a $2m property, and the cost segregation you got from a professional for the $2m property is $316k.