I'm not a money person. I deal with it only out of necessity. So say I have $1000.00 worth of Bitcoin and decide to enter the world of "mining". What's the physical process on my end and is there any guarantee that I will come out ahead?
There is no guarantee of profitability for any miner. What's more is that it is extremely difficult to estimate how profitable it will be because there are unpredictable variables involved. The mining difficulty is regularly re-targeted to account for increased mining power. The market exchange rate for BTC into dollars (or whatever currency your electricity bill is presumably paid in) fluctuates wildly, and the value of fees paid by users varies depending on mempool size or speed they wish to have confirmations. These variables are entirely out of anybody's control because they're a result of the actions of individuals.
Mining has been largely profitable due to the block subsidy which halves every 4 years. There is no guarantee that mining will remain profitable for existing miners when the next subsidy halving occurs (in 2021). If mining becomes unprofitable for them, they will have to scale back their operations or shut down and auction off their mining equipment. This will cause the difficulty to lower temporarily, which may make it profitable for new market entrants willing to take the risk.
Ultimately, mining is a risk-taking business and may never pay off. There are some obvious ways to try and increase your chance of becoming profitable though: Find the cheapest source of electricity you can and get the most efficient mining hardware for your price point.