Realize you may be better off using cost segregation to achieve greater tax benefits immediately for purchases of STVRs.

Roseville and Rocklin are great areas for long-term stability and growth, but the prices are quite high and the rents are LOW, and they're not friendly in terms of regulations for STR. 

When the lease is fulfilled, the security deposit will be returned to the LEASE SIGNERS, less any repair costs and unpaid charges.

They all lead to a significant negative monthly return due to one or more of the following reasons:1) Asking Price is too high2) Traditional loan rates (FHA and Fannie Mae) are too high and affect total debt payment3) Existing rents are too low, so loan underwriters won't approve.4) Market Rents aren't high enough5) I would like to use the minimum down payment with FHA (3.5%) or Fannie Mae (5%).So, from all of these attempts, my understanding is the only way to make a house hack work in this region where I would at least breakeven on a monthly basis, is to purchase at a significantly lower price, lock in a nice creative deal or bring up my down payment to at least 20%.

I am looking at structuring a deal and I'm worried the DSCR will be too low and the deal may benefit from restructuring by purchasing the 2 vacant out of the 12 otherwise occupied units with hard money as opposed to trying to purchase all 12 with a institutional loan just because I'm worried the 2 vacancies will drag down the DSCR for the new purchase.    

I realize there are better in investments, but we like Wildwood, NJ and would use it for 1 week during the summer and a weekend getaway during the off season.Current pricing appears to be $650-$850K for 3BR/2BA, 1,400 sq. ft. and ~$16K out of pocket costs ($5K yearly taxes, $10K condo fees covering wifi/cable, flood, sewer, trash, etc. and $600 for content insurance).

I am considering buying a starter home for my family (around $300k), living in it for a year, and then renting it out while buying a larger home for our family, like a 5-bedroom in the high $400k to low $500k range.

Cash for keys, while unpleasant from a moral standpoint, is often the better choice from a cost benefit analysis standpoint.

Your taxable gain / loss will be sales price less cost to sell less your adjusted basis.

@Kayla Palmieri read the contract or have your buyer’s agent explain thoroughly as some inspection contingencies require a licensed home inspector actually inspect it, and some even require approx cost of repairs and if seller agrees to that amount then you cannot exit for inspection contingency.