I definitely agree that rent by the room is awesome for increasing cash flow - again, it does come with it's headaches but with the higher risk comes higher reward (I've been doing it for almost 3 years now, it's really the only way to make the numbers work with little cash down on properties).From my personal experience, talking to others at meetups, and reading this post, I think there's definitely demand for specialized rent by the room property management.

STR can provide more cash (potentially), but its a high risk high reward strategy - if you invest in the furniture, staging, photos, and management or self manage, there is a lot of time and money invested.

No risk, just reward—whether for personal deals, joint ventures, or simply passing along awesome prospects to each other, I’m always actively prospecting for new deals and sharing them with my network.Let’s collaborate, learn, and grow together!

It targets individuals who understand the risks and rewards of income-based investments, rather than traditional property ownership.4.

I think there are two maybe 3 ways to look at this in my mind.  1) you go into it and bring it all up to modern standards but using that old charm to basically take what is there bring it up to modern standards and rent it out essentially I'm thinking cocktail bar or something trendy like that.2) most banks are on really good centrally located real estate if this is true, then I'd consider it for the dirt, plan to scrape the lot and go vertical with whatever the highest and best use is.3) a kind of combo of the two, if the lot is in a good location and its doable, pull the vaults or other "character pieces" out of the building, scrape the lot, and build whatever is best suited for the site there, but incorporate those historical pieces into the final designs.Is the site near a major retail area? 

You have to enjoy and reward yourself sometimes.

The bottom line is, the strategy can open doors you didn’t even know existed.. it’s not just a tax hack, it’s a wealth-building strategy that rewards a little patience and a lot of foresight.If you’re floating around Chicago, Omaha, or even dipping your toe in the Phoenix or San Antonio scenes, I’d love to help you navigate this territory.

I sacrifice today in order to reap the rewards in the future. 

Given your limited cash and high DTI, refinancing after boosting rents might balance risk and reward best.

@Steve Morris are you assuming the risk is high based on the reward?