Fear of a market crash, fear of negative cash flow, fear of humiliation by one's family "we told you it was a bad idea"The reality is, you'll hit some bumps in the road, but it is very hard to really screw up BIG with REI as long as you buy quality assets and don't completely fail at managing the property i.e. too lazy to fill vacancies..Ironically it is that fear that will make you buy a cheap property instead of a good one, because you "feel" that a lower price will curb your risk.And fear will make you accept a marginally qualified tenant because you are worried there won't be a better one next week.

Najeh,You will want to focus on investing in areas where basic improvements such as curb appeal and internal updates (ie kitchen/bathrooms) would support higher property values that you could refinance or sell to make your money back. 

Each tenant should be taking their own trash to the curb. 

As a result we can expect legislative initiatives in the future that place curbs regardless of legitimacy of any individual transaction. 

Also I have some ideas but not sure exactly how I would attack the bigger parts of the curb appeal (not talking about landscaping, I mean things like windows, siding, and support posts)

I made some nice curb appeal improvements, added parking spot rentals, added the U-haul dealer, improved internet presence, advertised in local papers and are affiliated with MySpareFoot.

Your curb appeal on your house will decline and if you live in an HOA be ready to get some complaints.  7.  

I suppose I could request all permits from the city and eyeball it from the curb.  

Usually a Land Loan is 50% of what exists- and you need a verbal nod from planning that septic, curbs, gutters, utilities, especially water, and the size of what you plan fits the neighborhood or general plan.A construction loan on land is a different thing.