You can vet attorneys and they have to consider the consequences if they give bad advice.

(REPS)A real estate professional for tax purposes is someone who materially participates in real estate trades or businesses, spending more than 750 hours a year and over half of their working time on real estate activities.

Idea is I could “trade-up” houses, get some trapped equity out of condo, and eventually keep this in my portfolio long-term, for a similar PITI.

It is a trade group for management companies specializing in residential property management. 

While DSCR loans focus more on the property's cash flow than your personal income, most lenders will still require a personal guarantor to reduce their risk.Keep in mind that DSCR loans typically come with higher interest rates than conventional loans, which is the trade-off for the easier qualification process.

Hi Jane--I'm a GC by trade who turned to flipping 3 years ago...Here is the skinny--it depends on these things. 

As a GC by trade, I have subs every week pushing to do more in a certain area saying 'You can just charge more for the house.' 

To qualify for REPS, the taxpayer must spend more than 750 hours per year in real estate trades or businesses in which they materially participate, and more than half of their total working hours must be spent in real estate activities.

For leverage of 50% or less any worries are psychological with little chance of consequences moving beyond the specific property leveraged. 50 - 65% could go either way depending on economic climate, specific property attributes, management, etc. 

The trade offs for getting in your first property are well worth losing the free rent with mom and dad in my opinion.