I have personally never owned a condo that DIDN'T have a special assessment - which happens when there is a repair needed but not enough money to pay for it. 

But for sure have an agent that is local do a drive by snap some pictures and give you a price assessment to see where your at. 

I feel, unless you truly detest your current work/life balance, or it has been you dream to be a part of REI, you will find it very difficult, if not impossible to build greater wealth from your position without significant risks and distribution to the stable family life you likely already have.You are not going to make compatible money from REI in the next few years.

I have seen people do this a variety of ways and you should assess it more on a case-by-case basis.

Should I subrogate for the sidewalk assessment and work done after I purchased my fourplex?.   

A Condo's reserve account only has to be 10% of their annual assessment income in order to be a Warrantable Condo for Fannie Mae or in general.

This helps you assess the buyer's creditworthiness and ability to make timely payments.

But, if the cost is fairly nominal, maybe under a couple grand, and you have no experience in real estate, including owning your own home and hiring contractors for that, then it is likely worth it.I would always start with a deep assessment of where you feel you don't have adequate knowledge.  

Assess your savings, budget, and eligibility for homebuyer programs.

I can't tell you how many properties have units easily convertible from 1 bedroom to 2 bedroom units, units with favorable dimensional standards which can boost rents with no photos to showcase these attributes, assessment square footage that is not correct,  upgrades not identified in the marketing materials etc.