You are in a position to handle the negative cash flow so that is not a concern.As you have likely already figured out, STRs have much higher operating costs (with PM) or take much more time (no PM), or a combination of the two, than LTRs. 

They fall in love with someone who's not good for them, or they settle for mediocrity, usually a combination of the two.

Another reason, and correct me anybody if I am mistaken, is that perhaps while constructing comps the owners and agents factor in sales of properties which were bought not for their cash generation as-is but because of zoning considerations that meant these parcels could be developed into something larger at a later date, perhaps in combination with properties and lots nearby that are already owned or were bought separately in different ways.

Unless there has been an extensive recent renovation, bump Maintenance and CapEx to 15% combined.

You could get questions from underwriting if you are combining your HELOC as the equity with a loan on the investment property. 

A key flaw your making in things is associating various markets unto each other, and things just are not that simple, the economy and GDP, stock exchange, commodities market, forex and real estate market have connections but are not tied unto each other and what affects one may affect another in various different degrees, or not at all. 08/09 collapse was a combination of bad speculative trading meet over-supply of real estate with a gravy coating of capital contraction.

We do have our trusts and wills set up, but I appreciate the offer.We just need to figure out the most efficient way to combine what we have while maintaining the flexibility to add to it in a way that will allow us to avoid reassessments and still allow us to get loans individually. 

I would appreciate if anyone who dealing or dealt with larger scale projects will advise me on this one.Now to the facts:Property type: ChurchProperty cost: $200k Development costs: $2.1M Number of units: 24 Average rent income per unit: $2,000Estimated total investment costs (including unforseen situations security): $2.8MEstimated annual total income: $576,000Estimated annual expenses + vacancy loss: $176,000Estimated net annual income:$400,000Estimated net ROI:14.28%Estimated time to end project:2 years ***The Property is located on a prime location in WB, PA***There are different sources of funding that I'll have to use for this project, which I guess it'll have to be a cash investor funding combined with banks / lenders money, so obviously I wont be a 100% shareholder.

For example, if you sell a relinquished property for $1.0 million with $600K in debt and $400K in equity you would need to acquire one or more replacement properties with a total purchase price of at least $1.0 million, reinvest all of your $400K in equity and then either obtain a new loan for $600K or put out of pocket cash into the transaction (or a combination of the two).  

More then likely setting aside the combined 14% for repairs is going to be overkill but its better to have it right in the beginning.