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With having young kids and working full time, being able to buy a house that needs mostly cosmetic updates that I can do myself would be easier than buying a property I would have to travel to without the family to work on. 

There are plenty of reasons, and a 1031 is really a lot easier than you think.

I prefer Kyle as i have done investment props on both areas and Kyle seems easier to rent out to me. 

Ultimately I've found it easier to just take ownership over any situation.

The more control they have, the easier it is for them to manufacture a dictatorial takeover.

If so, make sure agreement is in writing, signed by both parties, specifies new end date and ensures any existing security deposit will still be dealt with properly per landlord/tenant laws, and I'd also ask for a partial payment to be issued at signing to make obtaining his new place easier.  

Start with an easier and more realistic project.

So for a good deal flow you need to market, your farm needs to be several thousand units large.Frankly, it's a lot easier to become an agent.To that regard I’ve seen a real estate agent spend half of what it would have taken to built a profitable wholesaling business and become THE dominate agent in our city of 135,000 people.  

I have started using a spreadsheet but I would like something that makes it easier to keep track of when I have sent the owners a letter or postcard etc; also to attach a picture of the property and some pdf's of county record documents.