- when I allocate capital gains, gains and losses from sales, which accounts should those go to??

If you look at margins nationwide California,Parts of Florida,New York,etc. are all speculative.I remember a 4 or 5 years back in Miami there would be only so many condos being built and sold in a development.The investors would pay a homeless person (no joke) 100 bucks a day to stay in the line for them.They would buy up units and then immediately maybe in 1 to 2 months flip them for almost double.The markets were totally crazy then.Same stuff in Cali where brokers were telling me trailers were going for 750,000.So some of these investors that bought and made a ton along with foreign investors are ready to play the speculation game.They are not really in it for the cash flow.They already have a nice portfolio and chunks of cash to allocate funds to speculative investments and if they don't all margin out they will be fine.Speculating is fine if you have the money to lose and still be flush with cash.So these speculative markets have very wild swings in values.First to tank down hard and first usually to start going back up.In Georgia we have more moderate peaks and dips.So with some appreciation back but not huge swings in the future you need the cash flow as part of the deal.I don't like speculation just the hard numbers.I will speculate to a degree on land for future commercial development but I won't buy a house that loses money every month just on the potential of appreciation in the future.

But this is not a specific requirement.You can allocate the proceeds however you want in the purchases.  

Considering you need to allocate costs according to whether it’s your space, shared space, or tenant space.

I think that in order to feel confident about investing I need to spend about 4 months paying off debts (credit cards, cars) before I can reasonably allocate money to investing.

If it is a business that includes land/buildings as part of it (restaurant, factory, etc) then in a sale he can break out the real estate portion and exchange that for other investment real estate while paying tax on the allocation to Furnishings fixtures, equipment, and good will.All investment real estate is like kind to each other so a vacation rental is fine as well. 

Kinda piggy backing off of @Brian Burke's line of thought that you can always invest in the stock market and pull your cash out later.I look at most portfolio allocation decisions like this from the perspective of 1) Goals, 2) yield, 3) Risk 1) will not having enough dry powder available keep you from meeting your over all financial goals? 

I'm trying to determine the best way to allocate our resources to obtain good outcomes for each of my goals.

We just recently sold that property and reaped the benefits of having someone else pay down the mortgage for nearly eight years ;)  We also purchased a second home near Annapolis MD and sold that property for a profit as well.Now that we're in Charlotte, we're hoping to allocate some of our gains into new properties here. 

For instance someone that makes $1,500 per month and has rent of $500, allocates 33% to rent and had $1,000 to allocate to other expenses such as water, electricity, phone, food and other expenses.