Even if you want to roll the dice, at least is a calculated risk, not a surprise down the road. 

I recommend you budget 5% of the gross rent (for the whole place, even what the rent would be if you were living in it as a tenant) for repairs and 5% for capital expenditures.

If you want me to go into further detail, I'd be glad to do so either on here, via PM, or even just call me.

BP is not a great place to air out is this coach good or that program good.. as you stated 90% of the people on here are single minded they relate everything to owning a cash flow home and everything else is just gambling or guru speak or whatever..

Where would I even find a team? 

And this might indeed require some time to pass before doing that.You could still create a single member LLC with either you or your wife as member. 

New construction does not get a bump on appraisals.So for me buying an older home that I can fix up is a MUCH better value and I get instant equity when I buy and even more after I rehab the property.

Once you have a deal they will guide you through the process and even help you attain the funding with out coming out of pocket or using your personal credit.

You could do General Contracting where you'd need knowledge of all trades or manage a team of one single trade. 

Capital gains are calculated as:Sale Price - (Original Purchase Price + Capital Improvements + Selling Costs) - depreciation (if applicable) = Capital GainYour mortgage or HELOC balance does not affect this calculation—it only determines how much cash you take home after the sale.In Massachusetts, if the home was your primary residence for at least 2 out of the last 5 years, you may qualify for the Section 121 Exclusion, allowing you to exclude up to $250,000 (single) or $500,000 (married filing jointly) of the gain from federal capital gains tax.