There are some holes in the outer wall that we'll fix and will hopefully stop future water intrusion...but I don't know the climate well enough to know what is "normal moisture" in this region...Do these seem like "medium" priorities?

The wood is going to dry in no time if you have climate control, so it's not like you have to sit there waiting for a week to start putting up drywall.

Unfortunately, because of the inflationary climate we're facing, there aren't many safe havens to park your money short-term while earning a nice yield unless you're willing to do things like lend peer to peer but there's higher risk involved there.

Would really appreciate feedback of the best way to achieve hopefully both homes and different strategies for primary loans in todays current climate.

I’m starting to realize I don’t want to be in this state anymore and want to move to a warmer climate.

The aspect of cold weather climate, safety, and mismanagement as well as lack of jobs has kept me away.

I cannot report them for trespassing ...chicago finest will show up on that beautiful block on 70th and Damen and laugh in my face ..so will the tenants ..and I will only aggravate them to the point that they might trash the place once they will be forced to move out 1 year later by the Sheriff...1 year that's how long the eviction takes. first 90 days notice, then the sheriff need to go out there (who knows when) and give them the notice of forcible entry being filed against them then the judgment..then sheriffs eviction ..I will be lucky of they gone in Sept 2017. cash for keys will not work ...what they gonna do with $2K if they know they can live rent free for a year ...average monthly rent is around $800 over there ...good thing is ...that SFR 3br/1ba brick raised ranch will increase in value...I could make them my tenants ..have them sign the lease ...and hope they miss the payment ..problem is that once I make them my tenants I am responsible for upkeep of the property..what if there is mold in the basement and they develop sudden breathing disorder ?

However, having done and continuing to do a ton of research on this and other platforms, speaking and emailing with myriad RE Professionals from all over the Country I'm still not quite comfortable pulling the proverbial trigger.There's just too much hanging in the balance given our current economic climate nationally along with reliable and honest property management, maintenance and contractor pools in the local area. 

Also, if you see something looming that will affect your market, like a large employer coming to the area or announcing they are moving out of the area you should adjust accordingly for that too.Lastly, consider the political climate.

Between the population migration out of California plus the political climate being unfriendly to landlords, California isn't very appealing.