I want an air tight transaction and will have an attorney review and give me their seal of approval once I feel like I have thought of every possible negative outcome for myself.So far the possible negatives I have been able to think of are below and my intended solution will follow:Dodd FrankFinding a tenant without a license (I would like to market to those who have high days on market)facing penalty for performing broker transactions without a licenseI would market, find motivated seller, let them know that I can provide them with a cash offer, they can sell with a realtor (pay the commissions, spruce up costs, holding costs, etc.) or they can sell on lease option and get someone better than a regular tenant in the home.I would use standard docs specific to my state but they would be modified to include the below:Letter of IntentI would have them sign an intent to sell where in it, it would state that the property will be purchased via an option and the option will be in the name of a land trust.it will state that I as an owner and friend will be allowed to assist in the finding of a tenant, negotiate the lease terms, and be allowed to show the property without any compensation and at my own expense.LeaseMy lease will have verbiage stating that the tenant will be responsible for repairs, and normal up keep / wear and tear associated with the property up to $250 (this is my benefit I sell to the seller so that they don't have to deal with every tiny little tenant issue.Tenant will be responsible for all utilities and they are to be in the tenants namewill be allowed to extend twice, each for a period of 12 monthsTenant needs to inform owner of extension no less than 30 days before lease expirationthere will be no mention of the option within the lease, PITI will still be owners responsibilityWaiver of Liability associated with LeaseI will have a document created stating that the owner is solely responsible for the final approval, screening and placement of a tenant and that there will not be any recourse for myselfOptionFor the consideration of $1 (with receipt from trust to the owner) the trust will have the option to purchase the property no later than 45 days after the expiration of the lease.The purchase price will be agreed upon within 5 business days before or after the date of the lease expiration and if both parties are unable to agree upon a price, the owner and trust will each get their own licensed appraiser, average the two out and split the costs.this will be an option / right of first refusal hybrid and will very clearly lay out the expectations that there will not be any seller financing, the transaction will be in all cash or if the beneficiary of the trust so decides to get a loan from a reputable / licensed lending institution they need to provide a pre qual letter within 14 calendar days of the lease expiration and mutually agree upon a closing date.I would then sell my beneficiary rights to the trust for $5k, and exit the transaction.

I lean this way primarily because I can for the most part control the value through up keep and income.

The peace of mind of never having to worry about rates again is worth its weight in gold.

He's worth his weight in gold.  

My GC was the one who suggested tile given my concerns about upkeep, maintenance, and etc.At first, I was skeptical and not a fan of the tile idea (personal preference). 

The sewer line was apparently not built to code in the first place, but the drain line is starting to collapse under the weight of the neighbor's cars (they park mainly in the driveway but also in their yard directly on top of the sewer line).

(There may be longer fixed-rate products, I'm just not aware of them yet.)One advantage of 5-units and up, is that the appraisal will place more weight on the Income Approach.  

Do not confuse this with upkeep and maintenance requirements of your lease.

Some of us are heavily weighted in real estate, and we are extremely happy with owning this income-producing asset class.  

@Joe Villeneuve...you also make a good point about diversifying risk (don't keep all the eggs in one basket).On the risk side:- Property depreciation- Vacancies- General maint / upkeep required to keep the properties rentableObviously no risk, no reward.