Now, after doing this several times my success rate is around 1 out 5.   

First thing I'd do is check comps to get an idea of the demand and rates you can charge for your condo as a MTR.

This is most of the depreciation you are taking year one.You can calculate your depreciation recapture by taking the sale price of the asset and subtracting the adjusted cost basis.The adjusted cost basis is what you paid for the asset plus any improvements you made along the way minus the depreciation you took along the way.The profit above this original cost is taxed as a capital gain, but the part linked to depreciation is taxed at a maximum rate of 25% under the unrecaptured gains of section 1250.To recap the tax rates are:- Sec. 1250 real property: 25%- Sec. 1245 property and 15 year 1250 property: Ordinary Tax RatesThere are ways to minimize depreciation recapture especially if you know how to work smart with your CPA.1) Asset Valuation at Time of Sale - Sellers can minimize recapture by reallocating the price of the assets on sale.

I also wouldnt let your mom go into 2nd position on an investment property with any sort of restructuring; it doenst sound like she's in a position to risk being wiped out.Overall, though, if you want cashflow on the new property but cant achieve that after a refi into a market rate loan, it probably makes more sense to just flip it, pay off your heloc and your mom, and use the remaining capital for the next deal.

I don't think your first property needs to be perfect, but doing the work in advance gives you the possibility of refi (in a good rate environment) or more equity on a HELOC.

Do this hoping to keep your heloc balance below this number so you are paying less interest based on your average balance vs the rate of your first mortgage payment.

Your monthly corporate rental rate is $2800 per month and you have an 80% occupancy rate. 

Many of these lenders allowing 2nds behind them are more expensive capital (10's - 13's in our current market [high rates - but now showing signs of coming down]).

There is no stock account that gives the leverage real estate does, at as low interest rate real estate does, at as low risk/ volatility real estate does. 

Market insights and understanding the rental rates in the neighborhood.