I already have 4 SFH in Cleveland and would like to connect with more RE professionals including RE agents/brokers. 

I would call it a red flag if they resist giving you everything you request for your DD document list quite quickly, their speed and thoroughness in response to that shows their willingness to sell imho.When you schedule your inspection you want all your professionals there at the same time to go through a single time, contractor, inspector, and any specialists you think you might need like roofer, engineer, etc.Also don’t feel pressured to make your DD and inspection time as limited as is common in SFR, give yourself 2-3 months at least, again, from when they deliver the docs you request.Besides financial DD you want to do physical DD not just on the property via inspections but visiting the area during day and night, weekdays and weekends, to ensure you have a feel for everything that’s happening at different times all the way around the block.

I use TD Ameritrade Institutional which is carefully managed by a professional with a minimal fee structure.  

I think these older neighborhoods have a lot of charm and location convenience that young professionals and some "empty nesters" are looking for (Rosewood has the additional advantage of having a decent elementary school!).

Not sure if it’s professional enough.

He wants to also purchase his own home next year before his wedding, but again has no money for this, actually has a good amount of credit card debt.

It is a tremendous feeling because my whole life I could never find what I wanted to do professionally, and it brought many of draining emotions along with it.

How many people qualify as a Real Estate Professional for tax purposes?

-I want to look back and say 2018 is when I changed my life.I'm just sharing so I don't lose the motivation over the next year or two.So far I've just been saving for the wedding not investing yet.

Be firm and professional.