And @Andrew Beauchemin, your advice to build in some conservative numbers for volatility is sound.

You said you will self-manage but you should still plan conservatively and hold out 10% ish for PM.3.

However, if you kept good records and depreciation was taken appropriately, and you actually resided in each half of the property for 2 out of the 5 years prior to sale you should be able to take it all in the one sale with the exclusion.You would always have the option of 1031ing half and since your already contemplating a purchase it would be the conservative approach

I wouldn't assume that people would be willing to pay $700 for a room with shared bathroom/kitchen when they could rent a full apartment at a similar price.I would be on the lookout for more of a deal to ensure monthly rent is more than 1% of the total purchase+rehab cost and be more conservative in my rental income estimate. 

Am I being way too conservative in my assumptions?

Most of the rock bottom "for advertising purposes" stuff you see online has VERY conservative assumptions, with everything being 100% vanilla, which basically means only 1 in 50 can get what they advertise.

Depending on your mood at game time, you can play the game aggressively (take bigger deals earlier than you should) or conservatively (stay with smaller deals longer than you should) to contrast your various outcomes using play money rather than real money.

Although I think a conservation of some sort is the best option before eviction as paying late has been established as an acceptable behavior.

Then I calculated everything and was very conservative with my estimations.

I'm more conservative when it come to asset protection but in my opinion it's worth the money.