I suspect there are many moving parts in this deal that is sitting at the upper limits of DTI. 

They actually take up less space.1a - On the same theme (wallspace in the bedroom), move the bedroom door 2 ft away from the perp. wall in the upper bedroom.  

I'm just a normal guy, I'm not super intelligent, I didn't come from a wealthy background or have a leg up in this world.

My goal here would be to find a fixer upper, learn about rehabing, live in it (not sure how long), cash out refi (within 1-2 yrs) to recoup down payment, repair costs, closing costs, etc., and then later hold as a rental or sell.

Hey gang,  I know there's lots of Milwaukee cash flow investors on here, but I was wondering if we have any body that works the student housing and eastside (upper and lower) / Brady St. market on here? 

Check curtains, knobs, fixtures, legs on tables for looseness and so on.And this is a big one.

While it may not seem like a big shift from where it was a few months back (mid to high 3s) in expensive markets, it can really price people out quickly if they happen to be on that upper edge.I'm in The Bay Area, CA and it's been interesting to see the effect on availability, the days on market for properties.

A CONDO almost always has an HOA controlling the property (and interfering with your rental business)A Townhome is an architectural style:  living space on the ground floor and bedrooms on the upper floors, thereby reducing the footprint on the land. 

if it were me, i would put the new trailer in. i'd offer it to the upper end of the blue collars as RTO/LP. whether they exercise the right to buy or not, the "new-ness" can command a higher monthly rent/payment. if you can find someone to put a sizable down payment proving intent on ownership, they ought to treat the property better.3rd option, just offer the lot for rent at $300-$400/mo. they can bring their own trailer. if they ever leave, it should be in the lease that if they leave the home on the lot more than 30 days beyond their move-out date, the trailer becomes your. for free. clean it up and rent it out again. save yourself from spending 30k up front.just make sure your Monthly rent - PITI = cash flow. 

My thoughts: This is a lot more leg work upfront, but can be very rewarding.This same strategy would work even better if you can get it owner financed....lots cheaper than hard $ and typically won't impact any limit on the # of mortgages you can have at once.