I can honestly say I enjoy my job and don't plan on leaving it in the near future so this will be a side/retirement income generator for the time being but I'm all about opportunity so if I end up having a knack for this I can definitely see pursuing it more aggressively.I guess I'm reaching out to try and get in touch with investors in my area.

Now in my retirement, I am fairly certain I would enjoy staying in a tiny house to minimize costs. 

Austin Fruechting began buying rental properties less than 10 years ago, but by the age of 32 was able to retire on the cash flow coming in.

We had a plumber but he is basically retired - he has a partner that we have not used on any of our projects, but plan on using for our next plumbing issue.

I think that transferring the property to an LLC is a very good option for asset protection, especially since I own a primary residence, have retirement savings and other savings (for the next real estate deals!).

If the City skips a payemnt to keep teachers in classrooms next year, lawsuits will be filed by retired teachers worried about a CPS insolvency.  

@Tim PorscheAlso consider investing retirement funds into real estate.

Look for poorly written craigslist ads with 1 picture or none at all, those are usually your mom and pop landlords and usually older and ready to retire, especially if its a student rental! 

I'm thinking it could be something like "sell the property if I'm not able to have break even cash flow".Does anyone have any advice on when you should plan on exiting (other than death or retirement)?

I have been adding about $3400 per month to my mortgage for the last year and a half and will have it paid off in full in about another 3 1/2 years which is also when I plan to retire.