Based on your limited info my answer would be sell it, but it sounds like the trust or will is preventing you from doing that.

In the area where I would like to purchase next there is a conventional loan limit of $647,000.

It seems like in today's real estate market with limited supply, it is extremely difficult to appraise or accurately value a home (especially in New England/ Great Boston area where I'm from). 

@Gary Mazzarella for the most part land trusts, which are nothing more than a regular trust used to hold title to land, have been replaced by Limited Liability Companies.Before LLCs we’re available, limited partnerships and corporations where vehicles used but each had some negative tax consequences and ongoing costs and complications.

Yea, I was advised not to worry about the mold issue, its limited to small area. 

Crowdfunding through Reg CF isn't that popular in real estate because there is a limit to how much capital a company can raise.

However, after talking with a few people it sounds like we may have to also refi one of the properties (or both) as investment properties if want to still be able to reap the benefits of the low down payment conventional loan we've been using. 1) Is there a limit to how many times you can utilize a conventional loan if we are doing live in flips i.e. considered our primary residence?

You would have to do some testing on this, and also have backup plans for when the PM was not monitoring the radio.You should also talk to an attorney and your insurance company about what kind of language you need in your rental agreement related to having no/limited emergency communications as well as any other things they want you to do for this kind of situation.Hope that helps.Mike

You can do either.If you're just getting into the real estate game, then it's probably a good idea to speak with some lenders first as @Jaron Walling suggested.How far along you get in the process will be somewhat limited if you don't have a deal, but the conversations are still likely to be valuable.Additionally, some HMLs can offer a proof of funds, which can be helpful while making offers.Best,Michael

I know Dodd-Frank limits the financing of residential mortgages, but I don't think this applies to vacant land.