My risk is long term cap gains on about $500k so while it could be justifiable my alternative is to wait another two months to sell my home and receive full exclusion.

I know of people that have the credentials to do either, but will focus almost exclusively on one or the other.

The 2/5 year capital gains exclusion is great and could help you buy another deal.

If you are paying cash then time can become less of an issue but if financing raw land getting a tenant in 6 months can be way different than 18 months time because of increased holding costs.You need to check on deed restrictions and exclusive uses as you may not be able to do with the land what is it's highest and best use.

@Tim CriswellThere is nothing that would violate the tax rules in what you outline.You are allowed to administer your IRA, which includes making decisions, hiring vendors, paying the expenses of acquisition and maintenance of IRA assets, and receiving the income produced from investments into the plan.So long as all of your actions are via the plan, and for the exclusive benefit of the plan.  

I would recommend setting the LLC up in NY if that is where you will exclusively invest.

Aside the from the MLS, and resources exclusive to real estate professionalsWhat FREE TOOLS would you recommend to make comps in analyzing a deal?

Good residents that pay consistently and charging near market rent are not mutually exclusive...we can and should have both.Separately, my thought is to raise the one $50 annually and the other $50 semi-annually and provide plenty of advance notice.

Small business owners that use Schedule C to report their income and expenses as well as partners receiving a K-1, farmers filing a Schedule F and employees who aren’t provided a place to work by their employersPer IRS publication 587, To qualify to deduct expenses for business use of your home, you must use part of your home: Exclusively and regularly as your principal place of business; Exclusively and regularly as a place where you meet or deal with patients, clients, or customers in the normal course of your trade or business; In the case of a separate structure which is not attached to your home, in connection with your trade or business; On a regular basis for certain storage use; For rental use (see Pub. 527); or As a daycare facility.What are the allowable deductions?

Unfortunately no, you also have to have lived in the home for two years minimum, meaning you need to stay there until 1/30/2023 to qualify for another 121 exclusion.