@Travis Hintzel
Congrats for taking some action. You will learn a ton by doing exactly what you are doing...evaluating deals.
I wouldn't get too married to any potential deal. You can start justifying why it's a good deal and possibly blind yourself to the realities. You can't lose money if you don't do a deal. If it's good enough to be Warren Buffet's #1 Rule, it's good enough for me. Unfortunately, two of my first three deals were break even or lost money. I'm glad I took action because I learned some good lessons, but had I been a little more patient I would probably be a few years ahead of where I am now.
IMO you do not want to start with a condo, especially if the numbers are borderline. As @Robert Zuccaro mentioned, HOAs can be very political (I know from experience, I was VP of a 100-unit HOA for years). It can be like trying to tap dance on quicksand. Knowing what I know, I would never purposely buy a condo/townhouse as a rental. Not to say that there aren't those that are doing it successfully, but you had better know what you are getting in to. For example, NEVER buy a property with an HOA without having an accountant examine the HOA's financials. Most are woefully underfunded...see special assessments, below.
HOA Pros: Not many:
1. Overall your insurance will be lower, since the condo/townhouse HOAs typically cover the structure from the paint inward...with some exceptions, like what if your tenant leaves the water running and it ruins the neighbor's unit?
2. HOA fees usually include water and garbage, exterior maintenance, amenity costs (pool, fitness center, meeting rooms) but your should confirm what is included and what is not.
Cons: Many already listed by myself and others. But here is a huge one:
Special Assessments. These fun potential surprises can come up unexpectedly in the thousands of dollar range or more, depending. If the HOA is not good at budgeting or a large unexpected expense comes up, guess who pays? My HOA had to do a $1,000 special assessment to cover legal expenses that arose because neighbors couldn't get along.
A better option might be to find a 1-4 unit. No HOA fees and no HOA politics, more control, less surprises.
One way to go about finding a good deal is to run the numbers on 1-4 unit properties that you want in the areas in which you are interested. Decide on a Cap Rate that you are happy with (typically between 10-15%+, depending on the area) then make offers based on the value that YOU (not the owner, realtor) put on the property.
Good luck!
Peter