For instance you may want to limit the value of each to 1mm , which could be 10 properties worth 100k each or just 1 property worth 1mm.

Also, you are living in the property which should negate the limited liability of the legal entity (consult a qualified professional or two).Legal entities such as a LLC are not eligible for conforming residential loans. 

Not sure if its outside of the 3 or 6 years limit, but it will create another sale he/she should be reporting this year. 

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Mazzarella for the most part land trusts, which are nothing more than a regular trust used to hold title to land, have been replaced by Limited Liability Companies.Before LLCs we’re available, limited partnerships and corporations where vehicles used but each had some negative tax consequences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