I don't know CLE per se (I'm based in STL), but I know the financial side of gut rehabs in urban centers of big cities.

Bottom line, you have to decide how badly you want to own the place, and how much financial cushion you have, and how much risk you are willing to take. 

Just make sure to look into the HOA’s financials, rules, and rental policies before buying.

A good rule of thumb is to have at least $5 to $10K in reserves per unit to cover these situations and avoid financial strain.Thank you for the reply and help!

I think new builds in such areas is a great idea, but financially it's very hard to make the numbers work since you will probably have a very hard time finding comps.

Therefore, it is advisable for the client to consult with their CPA to receive personalized guidance tailored to their unique financial situation.

The real estate investing industry uses "Classes" to rank property performance risk, but there's NO agreed upon industry model:(Here's what we use for our Metro Detroit market:Recommend you first figure out the property Class you want to invest in, THEN figure out the corresponding location to invest in.Property Class will typically dictate the Class of tenant you get, which greatly IMPACTS rental income stability and property maintenance/damage by tenants.If you apply Class A assumptions to a Class B or C purchase, your expectations won’t be met and it may be a financial disaster.If you buy/renovate a property in Class D area to Class A standards, what quality of tenant will you get?

My goal is to create generational wealth for my family and to eventually have the financial freedom to say "yes" to travel adventures as a family. 

Consulting a tax professional or financial advisor familiar with these rules would be a wise step before making any decisions.

Even if I were to rent it out on Airbnb, the cash-on-cash return isn't very attractive.Specifically, I’m concerned about:High mortgage payments and the financial strain it could cause if the property doesn't generate sufficient cash flow.Cash-on-cash return is low, even with high-revenue short-term rentals.My Questions:Risk Mitigation:Any strategies I can use to mitigate the risks associated with owning a high-value property with a large mortgage?