Let's talk,DanIve actually been looking into buying a condo myself as an investment, I have a few rules, needs to be with both good hoa management & relatively cheap fee (bellow $600 a month) needs to be in area where I’m not competing against other new construction apartments, needs to be an area where even townhomes are so expensive you are not competing, I.e. upper nw, nova, Bethesda etc. needs to be 1990’s or newer in most cases.

There's no real hard and fast way or only 1 way or doing your first 2 points. your subject line suggests you're not looking to go to a large shop like a JLL or a CBRE which honestly I don't blame you those offices are usually pretty bloated.As far as monthly costs, if you are going to individually get a costar or other such license you are probably looking at $500-$1000 a month pretty easy in overhead once you have office dues, mls dues, marketing, etc. 

It's tough to compete with that as an investor.

@Andrew Kubik how's any different than a competent real estate agent who can provide the same connections.

Also, there is a lot of new competing rental supply coming online in these areas and a few of my developer friends mentioned to me they are seeing downward pressure on new build rents.

One huge benefit of a private/HML loan is the strength of making an offer when competing with cash buyers.

If your guests are leaving standard 5-star reviews, that’s great—but if those reviews could apply to any rental in your area, you’re still competing on price.If they’re leaving raving reviews, your property becomes the go-to choice—at premium rates.

To avoid non-competes and make twice as much, I wouldn't be getting a W2 job initially in Chicago and would rely on 1099 income.

Quote from @Trent Reeve: i would think they would have more amenities than a non-condo.I think the reference was how do you stand out from one condo to another when they are all identical, vs how do you compete with single family homes.

., I would do a search on here for Galveston and you will find some info.There are a lot of STRs there so you will be forced to compete on price so self managing is going to be the way to go.