Hey @Erik Lindquist for the most part I would agree with the comment below but as I just moved out of Marin county down to Silicon Valley it is a tough market up there.

Those are tough!

There are several markets that fit that criteria, but don't buy somewhere just because its cheap, you will end up with tough tenants and no appreciation. 

Now, friends and family are saying I am being too tough on the tenant A.

You're in a tough spot either way.

So, get your own estimates for the work.That said, every rehab is different and every rehabber is different, but I flip a lot of properties built in the 1998-2001 timeframe, and routinely do a lot more work than that:- Replace cabinets/vanities- Replace countertops- Replace appliances- Paint inside and out- Replace all flooring- Replace all finish plumbing fixtures- Replace all fans/lights- Replace front door- Replace any failed windows- Repair rotted/damaged siding, soffit, fascia, gutters- Replace all outlets, switches, plates- Basic landscapingWhile you may not *have* to do all that stuff, it certainly makes it easier to sell properties in this tough market...Btw, all that stuff typically runs about $20K in my area and with my contractors and basic level of finishes.

I think using those rent services to determine the amount to rent your duplex for is going to be tough in Oak Park as there are very few of them.

Geeeez, tough crowd! 

I also have weekly/monthly reporting calls with clients to discuss prospects and progress, if the listing agent disclosed you as a Buyer to his client and categorized it as a direct deal you have now put him in a tough spot with is client.

, yet I have no choice but to do just that on my next purchase closing Jan 2nd.We let go of one, and keeping the one that was open to our inspection visit, had the unit looking like we just walked into a catalog and appeared to have no issues making rent payments.The one we are letting go, gave us such a tough time at unit inspection despite being notified of this multiple times by seller’s team.I literally had to request my buyers agent to call seller agent back and ask that something be done to facilitate a thorough inspection, that “I was paying for”.About 45 minutes later, said tenant let us in and tried to play nice.By then sadly the damage had already been done and I truly have no interest in inheriting such a tenant.Long story short, yes I hate the “we have always done this, or we did this…..”