I am won't buy anything this year but rather next year so I am wondering if it makes sense to approach an agent or a lender months in advance, weeks in advance or only when I really already saw something I want to buy.I don't want to waste anybody's time and I am not yet sure what the best course is.

Of course, I'm out the deductible (2k).Incredibly, one week later, another 6ft diameter oak fell across the neighbor's front yard (this time, it damaged HIS house) and took down the power lines to my rental property which ended up causing just under $2000 of electrical work and tree removal expenses for me. 

Renting in these areas with a roommate or two will likely be less expensive than PITI in the 'less fun' suburbs.If you do decide buying when you move down here, I'd take a few trips and spend a week or so down here to help narrow the search.

The all-in podcast this past week just had a great discussion on this topic

-We are closing on a primary residence in a couple of weeks that has a cottage on it that we will begin short/mid term renting upon close. 

The first week they sent me a few properties on the MLS but since then it has just been me sending them properties I'd like to see and them arranging the showings.

All good until today, (2 weeks after signing new lease,)  he calls me and says he miscalculated his expenses, thought he could afford it but now he cant ect ect.

I hear similar stories probably about every other week here in Chicago, and I have had some situations happen to me during one of my early-on flips.Whatever you do , NOT take the low guy unless you are 100% certain they can complete the job.  

My monies would be invested in a group of six indexes named AIGO, AIPEX, BNPIMAD5, BOFANFCC, SPXFCDUE, and UBSIBAL.  

I am closing it in next 2 weeks.