-I don't save any additional income from my bi-weekly paycheck. Should I be saving more on top of my 401K?
>yes, definitely yes!!
-Am I relying too much on my 401K?
-Am I being stupid for counting my primary and rental towards my retirement? Meaning I assume they will appreciate and I will sell them after having accumulated equity.
>From a professional standpoint, yes, but it depends on how you look at your life and your goals. Going by the book, your net worth does not include the home that you live in, your furniture, or the vehicles you drive. (I am sure many will want to dispute this.) It does include investment property, investment vehicles (an antique car), other investments such as stocks, bonds, etc. When you decide to retire, you may sell your home and put that cash with your retirement funds, but you will still need a comparable place to live. You may like you house and neighbors so much that you may choose to retire there, if so what would do about that component of your retirement plan?
-What should I do with my 250K? I want to keep a chunk of that in cash for a rainy day fund but the rest I'd like to invest.
>Put a minimum of 6 months worth of your income into an emergency fund, which is to be kept in cash or as close to cash as possible (t-bills, money market, etc.). If your job is "iffy", you should keep more in the emergency fund. The rest should be invested. I cannot tell you what it should be invested in as I do not know if you are comfortable with the stock market or real estate, your risk tolerance, or many other factors.
-Should I pay off my rental which would create a $1K monthly income stream?
>It depends on how you look at life. Most accountants and investors will tell you not to pay it off. I would pay it off if it was my primary residence, but not if it is a rental; just my view. Just make sure you have an excellent insurance policy on that rental property, including lots of liability coverage, and make sure you have a cash reserve fund for it in case anything goes wrong.
As for how much to put into your primary residence and your remodeling projects, discuss it with your significant other, not with your friends. You should have a reasonable limit, yet the wants and needs of both of you should be met. How long you plan to live there should figure heavily into the equation.