Start off with a lower quantity and work your way up in the quantity. 

If you do I would love to hear it.Sell your ability to stay focused during stressful situations.

So this decsion plays a little into both trying to build a portfolio, but also finally having a place in where I'm originally from and often visit.I know I'd likely not see any cashflow from a Westloop condo, but I'm curious if anyone has any recommendations to lower my risk for the area.

Renting the home is high risk, Tenants do damage, stop paying rent, skip out without paying and create all sorts f stressful situations for home owners.

If it were a high end property it may be a necessity item but if middle or lower class it is a negative I personally would not consider investing in.  

@Bob Floss II I agree, one of the intermediate-term tailwinds of SE WI is the migration of some IL residents to lower tax areas, NW Indiana has also added residents from this trend.  

Investing can be very stressful so why have the other stress involved.

I look for 10% COC returns as you can see in the model and per my analysis, you would reach that by lowering your offer.AssumptionsDownpayment: 20%Closing Cost: 6%Amortization: 25 yrsInt Rate: 5.3%Occupancy: 90%Purchase price: $240kPurchase Price: $160k* I hope this helps and makes sense.

For example, is it smarter to buy a higher priced condo on the beach, or a lower price condo a few blocks away from the beach?

Profit margins, after paying lot rent, is slim but possible in the lower quality communities assuming lot rent is low.