If you're in a HCOL where homes are $300-400k+, there may well be flippers working on those high-end properties, but it's very difficult to cash flow a $300k SFR.

I'm going to start off by saying that I have yet to use private money in my career.

If not getting a loan will be difficult with that few years left because STNL lenders do not count options as the tenant might not renew.There is a lot that goes into analysis.

My first purchase was my most difficult and once I took that step I hit the ground running.

Purchasing an investment property increases the level of difficulty of your tax return.Purchasing a house-hack is even more difficult.To make it even more difficult - you plan to make improvements so you have to determine which costs are currently expensed and which are capitalized.Not only have you acquired an investment property but you also acquired a personal residence.As a result, direct expenses towards your investment property and indirect expenses are deductible business expenses that can be used to decrease your net income from rental activities.With all that is said - you are trying to operate a business so I would hire professionals to help you with your tasks.

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Eventually, I will transition out of my current job and into real estate as an active career.

There are many jobs/careers you can have that will help you learn about different aspects of real estate.

Arguably owning a hotel is much more difficult and they are going to be actual business owners.

The process of hiring the right contractor, permits, etc. was a little bit difficult but we found the right people and the city inspectors helped a lot during the whole process.