.- Its also my understanding, when working with the right lender and appraiser they can include the income of the property for the refi appraisal. boosting what you may be able to pull out on a cash out refi-  I am familiar with STR property management companies that will guarantee to increase your net while earning their split. helping reduce your personal labor.-  Another option you haven't mention...

My ultimate plan is to sell my lot to a developer who will likely construct a multi-unit- the lot is approximately 10k square feet and zoned for multi-units.The benefit is that they are paying the cost to build a new wall between the two properties, as there is no wall there currently.However, my concerns are (1) will this affect the future value of my lot- as the v-ditch encroaches onto my property approximately 12 inches, effectively reducing the useable square-footage of the property?

If the opportunity should present itself that a SFH pops up that I could house hack to reduce or eliminate my living expenses and save for another property, I've been considering doing that.

The utilities and so forth that you paid reduce your rental income but aren't part of the basis of the property. ie, they don't impact the sale price profit of the property.You probably should find a CPA that can help you sort all this out as it seems like you may need to file some amended returns to cover the period since you bought the property.

With RE investing you have multiple facets of gains (cash flow, depreciation/expenses (reduces tax bills), as well as long term appreciation. 

You are doing this to bc of your moms medical situation and are trying to set yourself up for the best start in the future.

Your post really shows how a little bit of knowledge and planning can reduce the tax burden... 

They could ask for an out if they're unhappy with her service, a reduced timeline, an exception if they are working with an agent in a different market or for a different product in the same market (example: one agent for their residence, a different one for an investment property), if they buy directly from their uncle who is a builder, etc.

It may be good to add provisions to your lease (perhaps you could require a medical condition be certified by a physician) so that all tenants are treated equally and you protect yourself from lawsuits.  

That just reduced the number of financed properties.If you're married, shove each loan into one spouse only.