Larger owners tend to analyze market rents monthly or even weekly and manage rents (or incentives) the best way they can.As long as the owner is engaged, the chance of adjusting rents is higher.

Not a chance.  

By the time a property is formally put up for sale in a town that size the locals have know it was going to be sold and had their chance at it.

I pushed the deal forward with multiple banks understanding that there was a good chance a banker would get pushback from underwriting later in the process.

I could put a down payment for a conventional (20-25%) 550k duplex, but I feel it could hurt my chances of buying as many duplexes in a 5 year period (for example) if I go conventional VS an FHA at 3.5%. 

This is true, but can increase your chances of success by working with an experienced team.Financing Challenges: Unexpected rate hikes or tightening lending restrictions can complicate your plans. 

Because, if you are a “regular” person meaning don’t make 5M a year W2 / legit bussiness which shows on tax returns, you can’t qualify for 20M loanAlso it mean, that people who buy 20M condo, chances are they have 100M-200M cash sitting and not doing anything.Return of equity is 0, as it also the cash sitting in a bank.Debt is cheap now days: 4-5%, but if you have “unlimited cash”, then not need to pay 4-5%As far as max cash flow and minimum risk - it’s something a lot of members discussed already.And last but not least - let’s not go off topic.

Residential at least has a chance of being profitable. 

If there is a high interest, cash flowing investment, 90% chance I already have money invested, so I did not see the need to pay for the coaching.  

I would say no-pitch meetups over a year would be the best possible chance to find someone who can be a voice of reason in your investing life if you don't have one.