They are there to build you into a stronger business person and leader, to open yourself up for MORE.It took me 4 months to get traction for my FIRST ASSIGNMENT DEAL (after losing everything in my first 5 out of state deals... if you haven't read the story, here it is again... ) , but once you learn and build MOMENTUM, things get easier and faster...until they halt again, as there's another lesson you need to learn as you grow into the next version of YOU, and YOUR BUSINESS.

I'm long DFW, San Antonio, and Houston real estate and will tap out when that transition has a stronger course and likely get a high(er) appreciation from it. 

While it is also true that Chicago leans tenant friendly, you can mitigate a lot of that risk by investing in areas that have a stronger tenant base.

Personally, I think there are stronger markets.

You may want to rent it out and wait until the market gets stronger.

Also, how can I make my offers stronger and attractive?

I feel like any time I spend showing homes, makes me a stronger agent in the future because I'm better at comps for listings and know the homes before I get my other buyers in them.

@Russell Brazil  definitely regionalized... in my two markets were I build new construction Charleston SC and Portland Oregon.. long gone is the no money down buyer.. they still happen I just sold one in Charleston on a VA loan but its a 350k house. and we get the occasional FHA but on the subdivision I just built in Portland in 2016  27 new homes priced from 330 to 400k... ( entry level )  to first time move up.My wife is my broker ( always recommend anyone getting in the business to have their own license) I had her run a report on financing and what was used.4 sold for cash1 VA3  FHA minimum down19 sold conventinal with 10% or more down.IN charleston other than the one VA loan same thing some cash a few FHA majority conventionalso to speak to your points we have a much stronger buying segment than pre 08.. and I am sorry for those that have crappy credit and can't buy right now.. but they simply need to clean up their act. this attitude that every american deserves to own a home is flawed thinking.. every american who can manage thier personal credit and keep good an stable jobs.. deserves a home if they so choose.. 

I use the LOC to make the offer, which makes it stronger than a offer with a contingent on loan qualification, and just buy it with the LOC.

Banks can't get out of their own way in order to close faster than 30 days.This is quite true, but what is somewhat ironic and comical is that the bank as seller will find an offer with a short closing time to be a stronger offer than the offer with a longer closing time; then once under agreement the settlement will get extended as needed by bank asking for amendment to the agreement via an addendum.