One of them even had the audacity to ask me to have my employer provide a letter explaining why they gave me such a large pay increase last year and explain that it was worth it.

Looking back: as a landlord its made me more aware to keep window sills in older units cleaner and I always employ a wet dry vac to clean window sills out before I give keys to a new tenant when doing turn overs on apts.

Not having seen it, I can also see where the IRS would be interested in fair market rents as to taxable gains or taxable amounts of benefits not being paid for, much like an employer providing housing and the employee not claiming that benefit, probably along the same lines.....And, there are different tax treatments for financed transactions, so there is another tax issue I can see.

On the personal side it is considered self employment income but I would recommend speaking with an accountant, they are usually very familiar with situations like this and can best provide you tailored advise

I am a former Mortgage Loan Officer who is currently employed as a supervisor in logistics working for a hospital chain in the Hampton Roads area of VA.

Comps, zestimate, etc.) you employed), Distributions (how investors get paid back), and any other Notes that may apply.I'm liking some of these more conscice, online methods over the more traditional but vebose, textual, "3 ring binder", more formal presentations I've done in the past.Example: http://patchofland.com/investments/beautiful-suburban-georgia-rehab.html

However, I'm not signing as an 'officer of the corporate employer' - I'm signing as 'plan administrator' which is me the individual, who is an account holder.Any ideas of where else I can go for a medallion?

I would include some reasonable dollar value for deferred maintenance as part of the purchase price calculation as it sounds like a new owner will probably have some work to do despite the tenants apparent desire to remain.What happens in the first couple of months that the tenants decide they don't like the new owner, have a change in employment status, or any number of other things that can cause them to move out.

My employer offers a generous retirement plan: 4% company contribution (regardless of whether or not employee contributes) PLUS a 5% company match.

If so, you buy in Teddy LLC, and then sell to Teddy individually, the spread will be taxable ordinary income plus self employment tax, as the profit passes thru the LLC to you, unless the LLC is taxed as a Sub S.