Seeking Advice: Sell Condo or use as first investment property?

[Frank Pilipauskas]

Hey BP!

I have been reading everything I can get my hands on for the last year and have a decent cushion to pursue my next property with the goal of 15-20 cash flow properties. I did not stumble upon BP until after my purchase of my Condo, so I never intended on using my current home as a rental but i am debating if it makes sense. I live in a nicer B-B+ area in the south Suburbs of Chicago(Orland Park). My Condo has a private entrance, 3 bedroom 2 bath, and allows dogs with NO weight restrictions which is pretty uncommon around here. I currently pay around 1150 per month for Mortgage + HOA. Water is included, and I only need to pay for electric/cable. Based on Rentometer, other hotpad listings, and from what i've gathered from Craigslist ads I suspect I can get around 1500-1600 for my place. The issue I have is that because the Condo is all electric, the bill in the colder months is beyond outrageous for the square footage(around $$450) last month. The price for electric is low during the spring/summer months, but i am nervous that this would cause high turnover should I choose to pursue renting this out even if i make this known. I also have heard horror stories of special assessments and i don't really know how often these can come up. If i sell now I believe I can at least break even. Purchase price of the condo was 143k which meets the 1% rule, but I do not know if this also applies to Condos. I'd love to hear the communities thoughts on what they believe the correct course is.

With that being said, I am planning on purchasing a 2-4 unit property to owner occupy and house hack. Do I find the deal or the lender first? 

I really appreciate any input. Thanks!