Not having experience with Section 8 I cannot say with certainty that you would not pass muster with this property, however if the housing authority does do their due diligence on a property I suspect that any shortcomings will quickly become apparent and would likely sink your chances of qualifying that property for Section 8.

I hope BP improves the iPhone app soon.

We don't know what state you are in, but 99% chance these properties will still have the previous owner mtgs attached to them, so no one will get clear title. 

Chances are that even if the bankers don't invest that they probably work with a bunch of mom and pop investors and they can guide you in the right direction.

For your first time, you may not be able to ride for 20 miles or do hill climbs, but you work towards it and you improve slowly.

CA by any chance?

I find that a very common hurdle that beginners have is assuming what a lender will or wont do. you said "I don't even think I would qualify for a loan of 100K" which may or may not be true, but you don't KNOW. what you really want to do is ask a lender what it takes to get that loan, rather than assume you can't get it and then blindly try to improve what you think they need. does this make sense?

What I'm hearing is that you are selling two investment lots and want to exchange into an avocado farm and want to make some improvements to that productive farm. 

Your best bet is to find a multi-family property that is mis-managed, has below-market rents, or needs to be renovated; then you can take the steps necessary to improve its performance.

If I need to replace the roof on this property, chances are I'll need 2-3 years of that CAPEX number set aside to do so.If you're only socking away 10% of 500 rent, that is $600 a year.