So if I owner finance them I’ll be able to sell for 3x what I got for it plus interest is my thought process.

I’m still just trying to figure out the process and how best to reach our goals

still in process

(I've already started the process of becoming an MLO). 

Here's time & money an agent or PMC needs to spend to get a rental listed:1) Make sure it's clean2) Hopefully, take professional pics and just not use the camera-phone3) Take room sizes and note positives and negatives about the property4) Since most rentals aren't advertised on MLS, research multiple sources for rental comparables to determine rent.5) Write a GREAT ad for the property6) Syndicate or manually enter the ad on numerous websitesThen, once published for rent, how much time do you think they spend taking all the phone calls (most of them from idiots who don't take the time to read the ad), doing all the showings, chasing applications & supporting docs, processing applications?

It just happened that im in the process of purchasing 2 properties this month. 1 is a rehab, that I plan on keeping for my self for a bit then selling.. the other is an invest property non owner occupied thats a 3 familyThe rehab I need to purchase out cash 105k and another 15k-20k to repairThe rental property I need to put 25% down and closing is around 70kSo I need 175k to purchase and another 30k to repair both properties I have 90k in liquid in a savings account,  230k in a 401k made up of the funds and stock and about 330k in my companies stock account..My plan was and not sure if this is the smartest way .. hence why I'm asking here!

I own one LTR and am in the process of having an ADU built on my property close to Bethel Church's new campus.

I know that renting up your investment can be one of the most confusing and nerve-wracking parts of the process (especially in a place with as much bureaucracy and legal hurdles as Chicago) and am more than happy to talk with anyone about that.

Hi Michael-Great question and an important skill for investors to understand.I recommend the ABC's of Real Estate Investing by Ken McElroy and Ken's YouTube Channel.If you are an investor, I recommend finding and using a good property manager for your properties as soon as possible to maximize your return on investment and make owning as passive as possible.A good property manager is a key part of your real estate investing team.Get them involved early in the underwriting process of a potential acquisitions and the planning for adding value.To Your Success!

Once you start talking to more people in the niche, you'll get a better idea of the process and whether or not you want to pursue buying in this niche.