Hughes Private Capital offered a fund which was Guardian Fund LLC that purchased properties.

For example, I have repeatedly informed him of my very negative experience with ABC Capital Investments (still going on almost one year with no payments to show for it) and yet he continues to promote ABC Capital Investments in Baltimore and Philadelphia despite fully knowing that many people continue to have very bad experiences with them.

Quote from @JD Martin: Quote from @Jay Hinrichs: Quote from @Matthew Drouin: Small wine town is all I needed to hear.Seasonal tourism is usually not a great industry in which to build a sustainable business.There are probably higher and better uses of your capital near high velocity metro areas.We have small wine towns near our city in the finger lakes region of western NY.  

As a GC I'll still try to negotiate a DP, perhaps only 5-10% (maybe even less depending on contract value) in this arrangement, but it's def not a deal breaker if those terms aren't incorporated into the contract since the largest capital outlay is not part of my scope.

If you do a 1031 exchange, you can defer both the capital gains tax and the depreciation recapture, which is a nice benefit.

In addition, 1031 Exchange Qualified Intermediaries are generally not required to be bonded, insured or maintain any other form of minimum equity capitalization.

Debt is going to make up 70%+ of your entire capital stack - it's critical to find the best loan/lender with the best terms possible. 

Expenses for initial repairs before renting are usually capitalized and depreciated.

In your second scenario you would eliminate all capital gain and depreciation recapture with the step up in basis.there is no statutory holding period that qualifies you to convert the properties. 

Primary Residence is taxed as short-term or long-term capital gains on sale and it may qualify for Sec 121 ExclusionIf you are classified as a Dealer you will pay ordinary income taxes on sale.