With over 60 units the software's I use are not a fit for you, but I would look into Guesty and BeyondPricing - those are what I used when I had a smaller portfolio under management. 

I’d like to establish a small-medium sized rental portfolio in the near term, and expand to commercial/large scale once I’ve got down the fundamentals.

Congrats and good luck.I'd recommend against a syndication on a deal this size because you can expect the costs to be $10K+, which means you are giving up a large % of your profit to legal fees.

However, think about another bath if you can fit it.

So I feel it's not a fit for everyone.

I agree with just paying the tax and don't try to force something that might not be a good fit.

Here is my $.02:  I don't know where you are located or the size of the parcel of land, but this is what I would do:1. 

When joining a mentorship program, it's important to ensure that the program is a good fit for your goals, needs, and expectations.

There is not a one answer fits all 

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