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You ask how to know if a business expense is a write off or not? The starting point with the IRS  A. Is the Expense Ordinary? An expense is ordinary if it is common and accepted in your trade or business. Example: If you run a web design business, the cost of software subscriptions (like Turbo Tax) is ordinary because most business use tax software. B. Is the Expense Necessary? An expense is necessary if it is helpful and appropriate for your trade or business. It does not have to be indispensable or absolutely required; it just has to be beneficial to your business. Example: A marketing campaign is necessary because it is helpful in generating customers, even though you could technically run your business without one.   To invest in the business or contribute to a retirement account? Short answer; contributing to a retirement account could possibly provide a deduction  while investing in the business as a capital contribution is not tax deductible but the use of the funds could possibly create a business deduction. Here is an in depth articles that you might find very informative and helpful with your questions about is it deductible for a business. https://turbotax.intuit.com/tax-tips/small-business-taxes/taking-business-tax-deductions/L5RueYPVS?priorityCode=3468337910&_gl=1*23rexu*_gcl_au*MTYxOTIxOTkwNC4xNzYyOTc2MjAy*_ga*MTU4NjQ3NDE0My4xNzYyOTc2MjAx*_ga_J7JHVCT5CT*czE3NjI5NzYyMDEkbzEkZzAkdDE3NjI5NzYyMDEkajYwJGwwJGgw Here is a number of calculators that could assist you in your calculations https://turbotax.intuit.com/tax-tools/  

There are other factors to consider as well before deciding on SEP IRA or Solos 401(k). A SEP IRA does give you flexibility in contributing one year and not contributing in another, you cannot take a loan from the SEP IRA. You will also have no Roth option with a SEP IRA. Solo 401(k) is only there if you are the sole employee of the company. You can easily open and manage a SEP IRA yourself. Most brokerage firms will handle the back end forms and requirements while you manage the investments, like a regular IRA. Whether you use someone to manage the investments depends on your comfort and knowledge of the investing. The contributions do not have to be made quarterly or throughout the year. They can be made at the year end or by April 15th tax filing deadline to be deductible from your tax return. You can also make them in small chunks during the year if you like. I would recommend making the complete contribution before filing the tax return.