I have found about $200 a month averages out their cost over time for big ticket items and even for smaller more frequent repairs. 

I'm a fan of the suburbs surrounding MKE as well.

I'm a fan of renting to pets in houses and duplexes, and perhaps cats if it's an apartment with no common area (with a limit of one).

As for my thoughts on it, I'm not a fan of investing in something that isn't going to cash flow, but if you have really good reason to think it will gentrify, it may make sense.

I am a HUGE community bank fan and anyone who wants to do this for any length of time I encourage to go find your banker and start that relationships up,, and then let it germinate..

I go to Norfolk frequently for work (DoD civilian) and would like to get to know this market. 

We have tried these methods also and weren't exactly a fan- Absentee owners with Equity.......

Personally, I'm a big fan of passive income and cashflow that shows up each month.You can also check out the local meetup for local investors. 

Here are some other things that could go wrong which may cause failures:Unknown necessary repairs (i.e. sewer lines, roof, etc)Not having cash reserves to cover vacancies / major repairsUptick of crime / vandalism in neighborhoodVandalism of propertyInfestations (pests, other)Bad tenants / No tenants / tenant family issue impacting stay (i.e. death, divorce)Rezoning of school districts / Loss of accreditation of school district Insufficient Property Management (not addressing tenants concerns, no notification of repairs timely - causing further damage, etc)Not following market pricing on rental / raising rent to frequently or too much at onceLegal issues (i.e. tenants sue for injuries on property, taxation, etc) I think you get the idea.

Hi Daniel, Absolutely, I frequent Boston's back bay several times each quarter for corporate meetings.