If your strategy is to create long-term income producing assets, you should definitely sell.If your strategy is to gain as much equity as possible by X date with as much certainty as possible, given the property's track record, you should probably hold until you get to that date.

Does it produce leads?

Putting a property under contract that's zoned R2 (has two rental income-producing properties) and need to do my due my diligence on getting the necessary variances to build 12-15 multi-family units.

Order files extended  and suddenly the sawmills had to start producing more lumber and plywood.

@Tristen M Walker I would start by thinking about the types of investments available to you and what returns they might produce.

Apartments are what a lot of people are trying to get into because of the scalability factor as well as the amount of cashflow an investment group can produce through the asset.

If your first deal goes well, and you're producing great investment returns, then go ahead and use retirement funds.

If an IRA investing in a mortgaged property produces better returns than that same IRA is producing today in terms of both principal security and return on investment, then that is a good investment for the IRA.There are other ways to invest an IRA that may not look so negative to you as compared to what you may be able to do personally, but then the IRA is not you - it is tax-sheltered retirement savings for your future self.  

Appraisers are slammed and not always producing the most accurate reports, so you need to be willing to pivot if you get a bad one. 

About meTop Producing Real Estate Agent for last 3 yearsHave a experienced flipped mentoring me Read everything I can get my hands on about flipping :)Tend to be a bit risk adverse with my numbers