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.

In addition to the local market appeal of Manhattan being a major employment center, a destination frequented by tourists, and severely space-constrained, international investors (the Chinese in particular) like to hold NYC real estate as a place to park their money.

I was recently let go and I realize that I want to create multiple streams of income for myself rather than relying on an employer.

After verifying his employment and income at a job he has held for over five years I feel confident in offering the house to him.He is happy and says that he will meet with me on the weekend (almost four days away) to sign the paperwork and pay deposits, etc.

Just make sure you understand the employment driver and it’s not just a one or two pony show in town.

I was considering the use of borrowing from my 401k with my existing employer as part of the non-retirement since I can't move that money but was hoping it could be combined with the self-directed. 

The IRS recently provided guidance regarding eligibility under the CARES Act and specified that a qualified individual includes an individual who has a reduction in pay (or self-employment income) due to COVID-19.Distributions:If so, you can take a penalty-free distribution (as well as waive the 20% withholding requirement) from your 401k (assuming that the employer allows it) anytime between 1/1/2020 and 12/31/2020.