In Mass there are a few operators that train/jv with students and might be worth testing out on them as well. 

However, given our experiences thus far, we are of the opinion that having more cash to operate with is a priority. 

Yes, you can its called Virtual wholesaling.

He has agreed to do the day-to-day management of the property (long term, as I accumulate more assets, I would consider hiring a property management firm).Looking to get some advice/call out any pitfalls in my assumptions:Focus on low cost, 55+ communities in Boca Raton/Delray Beach Area (Century Village, Kings Point etc.)Setup an LLC with my dad and myself listed (otherwise, my options to purchase in 55+ communities would be limited)Properties must have a net operating income of $1,000/month or more, expected rent $1,600-$2,000HOA: $450-$550, Insurance: $50-100, Taxes: $50, Maintenance: TBDInitially pay for all assets in cash, no debt. ($40k-$100k purchase price)For the first investment only look for minor cosmetic upgrades.

Rhonda, how long have you been operating the short-term rentals in Sevierville? 

As of today, 1/7/19, the IRS is juuuuust operational enough to be starting into the backlog of 4506-T transcript requests. 

The investor I work for no longer wants to become an employing broker so I can hang it with him due to fees, required continuing education and the fact we simply can operate without.

It's completely dependent on negotiation -- between the operating partners and the capital partners.Typically what you'll find in similar situations is either an LLC or an LP taxed as a partnership with a strong operating agreement in place that spells out income/loss allocation. 

As such you should operate your business in a way that makes sense for scale. 

Our company will also be operating as a relocation real-estate service helping our many large corporation in the Seattle area find housing for their employees relocating to the area which will benefit both the property management and sales division.