That trend will persist in future stages and you're about to entry unrealistic expectations territory.

Sort of goes with the territory, though.

This is my first time working with an agent and this would be my first real estate purchase so this is new territory for me.

Once your credit crosses into 700 territory you're basically going to get the best rate you can.

I see "stabilizing" characteristics in the $300k+ territory. 

If I could not attend a first time buyer's inspection on an iffy house I would most likely trade in a favor for another agent to be there, for questions for my buyer's, or to give me feedback...our market's "first time homes" are getting higher and higher priced = lesser and lesser affordable homes... fully believe it's our fiduciary responsiblity to help our clients in foreign territory!

That just goes with the territory.

At a 5% downpayment, the monthly total payment is ~5k and perhaps the rents could be increased a bit but even then, they'd only be around 5k total monthly gross rental income..after any expenses and repairs you're in negative territory. i don't really understand who would buy that property..I guess an owner occupant who doesn't mind having a higher personal monthly payment still, or someone just seriously banking on appreciation and willing to incur negatives during the meantime which seems silly..but i agree with the original poster that lots of multis in these areas (wicker/logan proper/humboldt) are priced like this kedzie one and basically aren't a good deal sadly, since they are the nicer properties (location and often turnkey wise). have to go further north/west to get the deals. im hunting for a 2-4 flat myself and wish it could be in prime palmer square location like the kedzie unit linked, but the numbers just dont work

It all comes with the territory.

@Frank GrecoWhile Florida does not have a state income tax; New Jersey(which I assume is where you live) does have an income tax.As a NJ resident; you are required to report worldwide income which would include the income from rentals located in FL.Having an FL LLC or a NJ LLC that registers in Florida will not change the above scenario.The good thing is that rentals often report a tax loss as a result of depreciation; but this is something to consider when you run out of depreciation and mortgage interest which may put you in the taxable income territory.