This is not an upscale neighborhood, plenty of people have average lawns, and the cost of re-sodding when it is time to sell is not that bad.

These will be my first two properties and it will give me a way in the industry, but I also don't want to make a bad financial decision.

Giving up so much money upfront is bad business. 

I think I've found what it is: International Paper Masonite Omniwood - the bad part is there was a class action lawsuit against this siding type, I think because of poor quality and not being able to stand up to the 30-year warranty.

A "simple" split in my county costs about $5000 (most of which is for surveying and plats) and takes around 4 months to complete - so not bad.

Don’t jump on a bad deal.

That isn't too unrealistic, if you have bad realtor and don't price it right the first time around...

Sure it's also a risk if you have bad tenants or the place catches fire but I feel it's a risk worth taking instead of watching your money suddenly either vanish or jump up.

For us, knock on wood, that's all you can do there and as long as your insurance doesn't kick you to the curb, you'll be fine.Biggest common risk I hear about is bad tenants ripping your places up and sucking away your time and equity. 

I am a local union electrician for Alameda county and have been building up a list of contacts of the tradesmen I met throughout my career and got along with on the job site, these individuals specialize in their own trade and are trust worthy people in general which was a big reason we got along.