Think about the first buy, how you'll pay for it, the rent you'll ask for, fixing up costs, adding value, what your family needs, where the home is, the rules you need to follow, how you'll handle it, keeping it safe, and being able to change with the market.

Also are land trust with nominee trustee as the attorney safe?

I've got enough depreciation to keep me safe for now, but that sounds like a good option to have. 

I am a Cash Buyer , Entrepreneur.  I buy and sell homes and wholesale Lease options . And I provide Rent to own homes for people with less -than perfect credit 

I had never missed a payment and had millions in total loans, so I thought that I was safe. 

As well as most folks are far to paranoid about litigation and liability when they are starting out. owning a SFR rental with proper insurance is about as safe as it gets with regard to liability as long as your not being a slumlord.

I couldn’t stand watching a portfolio of this size lose its relative value because it was 100% “safe”.

I added $20k to that to be safe and estimated $100k.I started at $330k and took off the $100k rehab and $10k carrying costs (interest only LOC and taxes, insurance, etc.)

Here's how it works in a nutshell according to IRS Pub 946.Consider depreciating rental property costs that may last > 1 year and aren’t eligible for De Minimus Safe Harbor (more on DMSH at a later time).You cannot depreciate the cost of land because land does not wear out, become obsolete, or get used up.

If it is normal and it's out of budget for you, you can either use financing to lower your cash outlay, partner up, or find a different property.If the work is cosmetic, it wouldn't be a big issue to tackle on your own, but if it's more than that, probably best to play it safe and hire out.