Hold it, rent it or sell it ? transition from condo to muti unit

[Ornuma Panmunee]

Hello. My name is Orn.

I'm having some difficulty making the decision and want to see what other options I have that I might miss.

Part 1 - the background story

I own a 2 bed 1 bath condo in Chicago since July 2016. ($147,500 with 20% down at 3.87500% interest. $336 HOA -- as of today the loan remaining is $106,050.53)

I love this condo. it great sunlight, the perfect size for my family.

YET, I'm not satisfied.

My goal is to become a landlord and start to invest more in properties by 30.
I was a stayed-home mom for 2 years and just back to work for 11 months.
The very main reason I'm back to work was that I want to make my goal happen.
(already 30 and still haven't made my goal come true. Eventho I have 740 credit score, still had some difficulty because I wasn't working long enough)

I got  2 pre-approvals

1. conventional loan for $299,900 with 5% down (only if I sell this condo or have a rental least. -- I might misunderstand in this one whether I have to sell my condo or not)

2. FHA loan 3.5% down. Max loan limit on a 2 flat is $ 461,000 on a 3 flat is $569,000

Part 2 - What I want

My goal is to own a multi-unit preferably north side of Chicago or Northwest of Chicago but open for any safe area for 3 years old boy and me who always gets home from work after 1 am.
(lived in Division blue line, Logan Square, Avondale, Old Irving Park, and now Lincoln square)

- Want a property that can stay rent-free or pay nearly nothing.

- Have tons of renovation ideas and would love to learn to do everything by helping, observing contactor (if they let me)
  I only know basic like paint, grout, change faucets, apply silicone, cut drywall, etc
  My end in mind is to be able to gain more skills and knowledge.

Part 3 - My limitations

1. I only have around $28,000 in saving

================================================================================================================

I put my condo for sell at $165,000. 2 weeks later got an offer at $158,000.
I was so ready to make a move to my next goal, so I accepted it.

Had the buyer came in for inspection. No critical repair but 16 listed of all cosmetic repair.
I agreed to fix some but not all. Now just waiting for the buyer to respond.

This is when I became to realize, I'm losing money in this deal. (sale commission is at $9,955 - 6% plus $475 for photos)
It's ok. it's happened. 

Questions :

- Is there a chance the buyer will deny and won't buy my condo? if that's a case, what will I lose besides having to start over?   

- What if I want to break the contact (not selling to that buyer), how much it cost? and what're other consequences?

- let's say I'm not selling this condo anymore and decided to put it for rent (between $1,400 - $1,500) Can I take out this condo home equity line of credit for next property down payment with the loans I got pre-approval? is that a thing?

- Do you suggest me to refinance?

- Ok, if the buyer agrees to buy, the closing date is on January 15th. I been searching for deals but haven't put any offer because my realtor told me it's no point to do it now, I should wait until the buyer is finalized. I don't want to hurry to choose just because I don't have a place to stay after the 15th. (I start packing and ready to move my stuff to self-storage unit I rented.)

- Is there other loans option I should look into?